335 Bear Trail at Bear Crossing

If you have a passion for cooking, the chef's kitchen on the main floor will truly delight you. It boasts a top-of-the-line gas range, stainless steel appliances, granite counters, ample counter space, a bar, and an open concept design. For those who prefer grilling, a gas grill is conveniently located on the covered deck. The open floor concept seamlessly connects to a spacious dining table that comfortably seats 9-10 people. The living area offers a gas fireplace, a flat-screen TV, and large windows that provide a stunning view.

Heading upstairs, the primary bedroom is nothing short of grand, featuring its own private balcony, a gas fireplace, a TV, a king bed, and an en-suite bathroom with a vaulted wooden ceiling. Just a few more steps up the stairs, you'll find a guest room with two twin beds and its own en-suite bathroom. Traveling downstairs, past the second living area, you'll discover another guest bedroom with a king bed, gas fireplace, en-suite bathroom with a soaking tub, and a walk-in closet. With each bedroom having a private en-suite, guests will experience a sense of privacy, comfort, and flexibility akin to staying in a primary suite.

To ensure an extra clean sleeping experience, this property follows the Triple Sheet Method, using two sheets to encase the comforter. The sheet-made duvet cover is washed between each and every guest.

For added convenience, a washer/dryer is available in the unit (detergent is not provided). An attached single car garage allows you to keep your vehicle sheltered from the elements.

We want to ensure our guests' comfort during their stay, and though this property does not have air conditioning, we have provided fans in each sleeping area to help keep you cool and comfortable throughout your visit.

Now, let's talk about the location. Winter Park Resort is a mere 4.4 miles away, and the FREE resort shuttle will conveniently drop you off in the heart of the resort base village. There, you can indulge in skiing, snowboarding, mountain biking, snow tubing, hiking, ice skating, shopping, dining, scheduled entertainment, and various summer activities. The Grand Park Rec Center, situated 1.9 miles away, offers multiple swimming pools, a waterslide, a full gym with an indoor track, a massive rock climbing wall, a gymnasium, and a children's playground. Next door to the Rec Center, The Foundry provides additional entertainment with a bowling alley, movie theater, and brick oven pizza bar. The nearest grocery store is located 3.8 miles away in the town of Fraser.

For the comfort of all guests, smoking and pets are not allowed on the property. Enjoy free Wi-Fi throughout your stay.

Make Bear Trail your next vacation destination; with its unbeatable location and amenities, it promises an unforgettable experience!

As responsible hosts, we strongly encourage guests traveling to Grand County to stay informed about the latest updates regarding fire restrictions. Open fires are not permitted on the property, but you are welcome to use the propane BBQ.

Winter Park STR # 007164

Vacation Rental Reviews

• Fantastic Views! Clean! Perfection.

  Stayed 5 days ending in April, 2024

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  a guest from Jackson, MO recommends this vacation rental

  I had saved a hundred options for our stay. My husband finally helped me choose this one. It seems you always take a leap of faith. This one was the real deal. It was exactly as described. The views were picture perfect out every window facing the mountains. The size was perfect for our family. This condo was more than I could have expected. The kitchen was well stocked for cooking meals. As a picky customer, this condo far exceeded my expectations. Responses were fast to questions.

  • Manager Responded on 4/5/2024

    Thank you for choosing to stay with us! We're thrilled to hear that our property exceeded your expectations and was exactly as described. It's wonderful that the views were picture-perfect and that the size was perfect for your family. We're glad the well-stocked kitchen made meal preparation easy for you. We aim to exceed expectations, and we're delighted that we could do so for you. Thank you for your kind words, and we hope to welcome you back again soon!

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• Great place to stay in Winter Park

  Stayed 5 days ending in January, 2024

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  Reggie J from Mansfield, GA recommends this vacation rental

  Great communication! Great place to stay! We got snow dumped on us while we stayed and the management team sent a crew to shovel snow and offered to drive us.
  
  Only negative was the upstairs beds mattress was worn out a few years ago! Awful! Outside of that I would highly recommend.

  • Manager Responded on 1/15/2024

    Thank you for taking the time to share your experience, and we're thrilled to hear that you found our place great for your stay in Winter Park. We appreciate your kind words about our communication and the efforts made by our management team to ensure your comfort during the unexpected snowfall. We apologize for the inconvenience caused by the worn-out mattress in the upstairs bed. Your feedback is invaluable, and we'll forward your review to the owner in hope to enhance the overall experience for our guests. Thank you for the recommendation, and we look forward to the opportunity to host you again in the future

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• Family Christmas 2023

  Stayed 8 days ending in December, 2023

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  Jodi C from JOHNSTON, Iowa recommends this vacation rental

  This was a lovely place for our family of 5 to spend the Christmas holiday! We enjoyed great skiing, winter hikes and hanging out together in this beautiful townhouse.

  • Manager Responded on 1/13/2024

    Thank you for your review! We're thrilled you and your family enjoyed your Christmas holiday at our townhouse. Looking forward to hosting you again for more great moments!

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• Summer vacation for large family

  Stayed 3 days ending in July, 2023

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  a guest from Grand Junction, CO recommends this vacation rental

  Excellent condo, would definitely stay there again. Comfortable beds. Kitchen was well equipped. Close to hiking, biking trails.

  • Manager Responded on 7/11/2023

    We're thrilled to hear that you had an excellent stay at our condo and that it provided a comfortable and well-equipped space for your large family. It's wonderful to know that the beds were comfortable and that the kitchen had everything you needed. The proximity to hiking and biking trails is a great advantage, allowing you to easily explore the beautiful surroundings. We appreciate your positive feedback and look forward to welcoming you back for another stay in the future. Thank you for choosing our condo for your summer vacation!

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• great 4th of July

  Stayed 4 days ending in July, 2023

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  connie c from BOULDER, CO recommends this vacation rental

  All in all Very good

  • Manager Responded on 7/9/2023

    We're delighted to hear that you had a great 4th of July! It's wonderful to know that your overall experience was very good. We appreciate your feedback and thank you for choosing our property for your holiday celebration. We hope to have the pleasure of hosting you again in the future!

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• Would have appreciated communication during stay

  Stayed 7 days ending in June, 2023

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  Ruth R from McAlester, OK recommends this vacation rental

  The rental property was great and easily accessible. We had everything we needed while there. Views are awesome! The bed in the upstairs master wasn’t comfortable but we managed. We would have appreciated a heads up about some painting that was being done on the condo so we could protect our vehicle by pulling it into the garage. The company didn’t communicate this was going to occur and the painters didn’t communicate that they were painting and needed our vehicle moved. So, our vehicle got red paint on it. Fortunately we walked out soon after and found it and was able to take it to a car wash and wash it off. Could have easily been prevented with some communication. Otherwise, a very enjoyable stay.

  • Manager Responded on 6/23/2023

    Thank you for your review! We're glad to hear that you enjoyed your stay at the condo and appreciated the beautiful view and quiet neighborhood. We apologize for the inconvenience caused by the unexpected maintenance and the paint dropping on your vehicle. We understand how frustrating that can be, and we apologize for not informing you in advance about the maintenance schedule. Unfortunately the HOA did not inform us about this. Had we known, we certainly would have given you a heads up. Your feedback is valuable to us, and we will work on improving our communication regarding any future maintenance activities with the HOA, to ensure a more seamless experience for our guests. Thank you for choosing our property, and we hope to have the opportunity to host you again in the future.

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• Don't rely on the pictures

  Stayed 2 days ending in April, 2023

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  Tim M from Centennial, CO recommends this vacation rental

  The pictures were nice, but the property so far exceeded the pictures. We were blown away by the cleanliness, quality and the great layout of the rooms.

  • Manager Responded on 4/24/2023

    Thank you for your feedback! We're thrilled to hear that our property exceeded your expectations and that you were blown away by the cleanliness, quality, and layout of the rooms. We strive to provide accurate and appealing pictures, but it's always rewarding when our guests find our property even better in person. We hope you had a memorable stay, and we look forward to welcoming you back in the future!

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• Excellent Condo for our Spring Break Visit

  Stayed 5 days ending in March, 2023

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  Marty W from Lakeland, TN recommends this vacation rental

  This condo meet the needs of my family of 4. Management company was responsive to all my questions/requests. Very easy check in and check out process. Garage was a nice bonus bc it snowed a lot while we were there. The 3 gas fireplaces were great after long days of skiing. The kitchen was an equipped with everything we needed stove, oven, microwave, fridge and all utensils.
  Negatives: 3 story condo that creaks. I’m an early riser so my family complained I woke them up walking around in the morning. You can definitely hear when someone walks or talks regardless of which floor they are on. Another minor issue especially if there is snow, it is a tight pulling out of the garage onto the road without hitting large snow mounds. Lastly, you do have to drive thru condo construction and we got 2 nails in the tires on our rental SUV.

  • Manager Responded on 3/19/2023

    Thank you for telling us about your stay! Happy to hear the condo had everything you needed. We will get in contact with the construction crews about cleaning up better. Hope to see you back at Bear Trail on your next Winter Park spring break trip :)

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• 3 Generation Family Vacation

  Stayed 5 days ending in January, 2022

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  Amy M from Van Alstyne, TX recommends this vacation rental

  We had a great trip! Everyone was so comfortable. Plenty of community space and as well as private space.
  All of the conveniences of home. I would highly recommend staying at this property.

  • Manager Responded on 1/3/2022

    So happy to read that you had a great trip and that you enjoyed the home and the location. Thanks for staying with us and taking good care of our property

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• What a view!!!

  Stayed 3 days ending in December, 2021

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  Michelle H from Auburndale, FL recommends this vacation rental

  This place was perfect for every member of the family. Space for all from the beautiful living room, spacious bedrooms, second living room downstairs, and three fireplaces. Loved the holiday decor which was perfect for our Christmas holiday. All was clean with a fully stocked kitchen. Would definitely stay there again and hope to return someday. On top of it all, the hostess Charlotte was super helpful.

  • Manager Responded on 12/29/2021

    We are thrilled to read that you truly enjoyed this gorgeous home at Bear Trail / Bear Crossing. Thanks for staying with us and for taking good care of our beautiful mountain home

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• Best Place in Winter Park!

  Stayed 12 days ending in August, 2021

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  Polly H from Fort Worth, TX recommends this vacation rental

  Top Notch Condo! Plenty of space to spread out with four adults and three kids. Gorgeous views. Love the two masters with king beds, three gas fireplaces that turn on with the flip of a switch! Kitchen has all the essentials. We spent 12 nights and fell in love with this place.

  • Manager Responded on 8/30/2021

    Thanks SO much for staying with us. We are truly happy to hear that you found a place that worked out very well for you and your family. Agree - the views are truly gorgeous from this property:)

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• Another wonderful visit to Winter Park

  Stayed 5 days ending in July, 2021

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  Dave V from St. Louis, MO recommends this vacation rental

  This is the 3rd year in a row that I have visited Winter Park with either my wife and sons or my brothers. This was a trip with my brothers. This was also the 3rd year in a row that I have stayed at this beautiful condo. It feels like home and it never fails to impress. Charlotte and Nick are really great to deal with - as usual!
  Highlights of this trip included Pikes Peak, Garden of the Gods, Rocky Mountain National Park, rafting the Royal Gorge with Royal Gorge Rafting, mountain biking in the Trestle Bike Park, hiking to the top of the Continental Divide along Loveland Pass......great activities! We enjoyed dinner at Randi’s (2 visits - try their meatloaf - excellent) and the Peak (the Ferg burger tastes great too)
  We all love Winter Park and will be back......and this property is the ideal choice!

  • Manager Responded on 7/9/2021

    We are so appreciative that you guys keep coming back each year and that you feel that the home is "a home away from home" Sounds like you had some amazing trips to some of the most beautiful areas here in Colorado. See you next year!

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• Nice Property!

  Stayed 5 days ending in June, 2021

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  a guest from Elkhorn, NE recommends this vacation rental

  Very good experience. Property was mostly clean, quiet and offered more than enough space for four adults and two children. Location was good, considering it was late spring and during non-ski season. Visited Grand Lake, Georgetown, Rocky Mountain National Park, etc. and the kids enjoyed two great playgrounds in Winter Park and one in Grand Lake. The accommodations in the home were excellent. Great views from the decks. No major complaints other than air conditioning would have a been nice, given, given the early nighttime stuffiness... but assume nobody has AC in ski land.

  • Manager Responded on 6/16/2021

    Thanks for staying with us. Glad to read that you had a very good experience and that you got to visit a lot of the local spots. You are correct, that there isn't any AC in any properties in the area (sorry)

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• Outsatnding!

  Stayed 3 days ending in January, 2021

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  Leroy W from Columbia, SC recommends this vacation rental

  This place is absolutely amazing with tons of extras! Perfectly located and I would recommend this place to a family or large group of friends.Manangement was very helpful too.

  • Manager Responded on 1/27/2021

    Happy to see you had a great time. We appreciate the recommendation.

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• Great property .

  Stayed 3 days ending in September, 2020

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  michael o from weatherford, TX recommends this vacation rental

  More that we imagined . Perfect property . Great neighborhood . Amazing view.
  We will be back.

  • Manager Responded on 10/19/2020

    We are so happy that this property exceeded your expectations. We thank you for the kind review and hope to host you again on your next Winter Park getaway.

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• Another great visit to Winter Park

  Stayed 5 days ending in August, 2020

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  Dave V from St. Louis, MO recommends this vacation rental

  After vacationing three times in Winter Park with my wife and kids from 2015-2919, I organized a trip for my brothers and me this year. I made reservations for the four of us in the same condo that my family and I stayed in last summer.
  What a great condo! It is a beautiful place with tons of room and premium appointments.
  Last year and this year, the condo was spotless and Charlotte and Nick are great to work with - timely and friendly communication. (This is the 4th time I’ve worked with Winter Park Management and each time has been great)
  This was a shorter trip than what I am used to with my wife and kids but was still a great time. Once again, we used Winter Park as our base to do lots of activities including renting a Jeep from Mountain High Rentals in Frisco (2nd year in a row with them - definitely recommend), went to Rocky Mountain National Park and then down into Estes Park with lunch at The Stanley Hotel (overpriced but worth seeing once), floated the Arkansas River thru the Royal Gorge (with Royal Gorge Rafting - 3rd time using them - great float with a great outfitter. It’s a serious float - go with Royal Gorge Rafting!) and then mountain biking at Trestle Bike Park in Winter Park (tough to match the combinations of trails, scenery and prices - rented thru the Trestle Bike Shop)
  We ate dinner twice at The Peak and twice at Randi’s Grill and Pub. Fantastic wait staff at Randi’s in particular. But we enjoyed both places.
  We love Winter Park and it feels like a home away from home in this condo. We likely will be back next summer and this is the condo we will choose!
  The only disappointment we ever have is that we have to leave such a beautiful place!

  • Manager Responded on 10/13/2020

    It seems you had quite the adventures during your stay here and it sounds like you had a blast!! We are so happy that you enjoyed your time here and we look forward to your next reservation with us!

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• Bear crossing

  Stayed 4 days ending in September, 2019

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  Diane S from Tecumseh, ON recommends this vacation rental

  This is a beautiful place to visit! The views from every balcony was beautiful! Very clean!

  • Manager Responded on 9/23/2019

    Appreciate you staying with us and taking your time to write about your stay. Happy to hear that you were happy with the property and that you got to enjoy the views from the balcony.

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• Great townhome!

  Stayed 3 days ending in September, 2019

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  Unkyong H from Longmont, CO recommends this vacation rental

  Impressively clean! Nicely decorated, comfortable, nice view, nice kitchen, good location with access to trails, not far from town.

  • Manager Responded on 9/23/2019

    Thanks for staying with us. Printed out your review and shared with our cleaners - to forward the compliment on the cleaning of the home. So happy to read that you enjoyed the house and that you had a great stay.

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• Outstanding property!

  Stayed 9 days ending in July, 2019

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  Dave V from St. Louis, MO recommends this vacation rental

  We stayed in #335 Bear Trail from 7/22 - 7/31 with our family of four (my wife and two sons -22 & 19 - and me). Winter Park is probably our favorite vacation spot in Colorado - we feel it’s the easiest “out of the way” place we can find - less than 2 hours from Denver and 30 minutes from Highway 70. This property was absolutely beautiful with great views, lots and lots of room, great furniture and it was spotless. We have used Winter Park Management on our last two visits and Charlotte and Nick have been great to deal with, I emailed Charlotte when we got home to tell her how much we loved #335 and said if we return to Winter Park next summer, we will definitely stay in this property again.
  One of the reasons we like Winter Park is it is a great staging area to cool activities within 2 hours of the unit.
  We did a cattle drive horseback ride in Kremmling, CO at the Rusty Spurr ranch which we highly recommend. You are also just 1 hour from the entrance to Rocky Mountain National Park. We did a whitewater float trip with Kodi Rafting out of Brown’s Canyon (4th time we’ve floated with Kodi they are first rate). We rented a Jeep from Mountain High Jeep Rentals in Frisco and drove some awesome trails around Breckenridge. Finally, we rented mountain bikes at the Trestle Bike Park in Winter Park. This has to be the best mountain bike park in Colorado - great trails and very reasonably priced compared with other places in Colorado that we have been.
  Bottom line - Winter Park is a great vacation spot for us, beautiful scenery and was made even better this time by #335 Bear Trail that would easily qualify as a dream vacation home!

  • Manager Responded on 8/12/2019

    Thanks for sharing your experience with us. We enjoy working with you and you always take such good care of our properties. We are happy that you have found your new home away from home, and we will look forward hearing from you again when you plan next years trip to the beautiful Winter Park. Until next time - take good care. Charlotte

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• Lovely vacation home at Winter Park

  Stayed 5 days ending in March, 2019

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  Robert G from Chesterfield, MO recommends this vacation rental

  This place was immaculate. Plenty of room for all of us. Originally planned on having twice as many staying with us but half the group wasnt able to make it. There were four of us that stayed here and this place could easily have accommodated 10 or more. If you are looking for a great place to stay this is it.

  • Manager Responded on 4/5/2019

    Thanks for staying with us and for taking good care of our property. Happy that you guys had a great time.

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• Excellent property.

  Stayed 5 days ending in March, 2019

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  Nathan G from Houston, TX recommends this vacation rental

  Excellent property. Clean, nothing broken, good layout, kitchen was very well stocked.

  • Manager Responded on 3/17/2019

    Thanks for staying with us and thanks for taking good care of our property. It is great to hear that you were happy with the property. Sounds like and looks like you had a great Spring Break in this beautiful home at Bear Trail

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• Beautiful accommodation stunning views very cozy

  Stayed 4 days ending in February, 2019

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  Elena T from Longmont, CO recommends this vacation rental

  We decided to make last minute plans to ski WinterPark. Not only is this place close to the mountain, but it was such a lovely home! It felt cozy, but luxurious! The beds were amazing. The kitchen had everything and then some. We loved the fireplaces in the bedrooms. The views were absolutely stunning. We will definitely stay here again!

  • Manager Responded on 2/22/2019

    Thanks for staying with us and for taking your time to write about your stay. Very happy to learn that you enjoyed the home in so many different ways. You are correct, the views are truly stunning! Glad that you got to experience the beauty of what Winter Park has to offer

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• Winter Park Trip

  Stayed 1 day ending in November, 2018

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  Daniel B from Fraser, CO recommends this vacation rental

  Thank you for an amazing stay!! WE loved everything about this condo and cannot wait to come back. Management was super helpful and easy to work with.

  • Manager Responded on 11/13/2018

    Glad you enjoyed your stay in the mountains with us. Looking forward to seeing you again soon! Take care!

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• Great!

  Stayed 1 day ending in October, 2018

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  Daniel B from Fraser, CO recommends this vacation rental

  We loved our stay at his condo! Had a great time in Winter Park. Booking and check in was easy. Condo was incredible. Everything we needed and will definitely be back.

  • Manager Responded on 11/4/2018

    Thanks for taking you time to write about your experience at this awesome town home at Bear Trail. Happy to hear that you enjoyed the property.

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• Perfect

  Stayed 1 day ending in October, 2018

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  Daniel B from Fraser, CO recommends this vacation rental

  We had such a great stay at this condo in Winter Park. Super clean and everything we needed was there. Looking forward to returning!

  • Manager Responded on 11/1/2018

    Thanks for taking your time to write about your stay. We are super happy to hear that you had a great time. Can't wait to hear from you next time you plan on visiting this beautiful property at Bear Trail!!

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