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Compare 1036 Vacation Homes in Gypsum with updated reviews, rates, and availability.

Mountain Gem Walking Distance From Slopes w/Shared Pool & Hot Tubs, Free WiFi

9.6 out of 10, Exceptional, (40)
"Nice to have the three bathrooms with all adults"
Mountain Gem Walking Distance From Slopes w/Shared Pool & Hot Tubs, Free WiFi

Game & Movie Rooms, Fire Pit, Family Friendly, A/C

10.0 out of 10, Exceptional, (87)
"We stayed at the Bennett House in January, 2025. There were enough beds for seven people very comfortably and lots of room for meals and entertainment. We really enjoyed the movie room and game room - lots of rousing air hockey and foosball action! We would definitely stay there again in the future! "
Game & Movie Rooms, Fire Pit, Family Friendly, A/C

Modern Seven Castles Basalt Home

10.0 out of 10, Exceptional, (17)
"Stunning views, beautiful interior super comfy! Great space for enjoying family and taking in the Aspen area. Highly recommend! "
Modern Seven Castles Basalt Home

12MM Aspen 5BR New Construction Residence in Town by GuaranteedRental

9.6 out of 10, Exceptional, (50)
"Prime spot with views and close to town. Our group had a fantastic stay. "
The price is SAR 7,316
SAR 12,210 total
includes taxes & fees
18 Feb - 19 Feb
12MM Aspen 5BR New Construction Residence in Town by GuaranteedRental

2 Bedroom + Loft, Right on Gore Creek, Free Bus Route, *New Listing*

9.2 out of 10, Wonderful, (32)
"We found the property easily and enjoyed the organic location near the creek. It was a little snug for our group but met all of our needs while we were in the area for baseball events. We were required to complete and sign a bedding configuration days in advance, however, it was not done. We made do and otherwise, enjoyed our stay!"
2 Bedroom + Loft, Right on Gore Creek, Free Bus Route, *New Listing*

504 | Luxurious Beaver Creek, Ski in/out + Ski Valet, 4 Season Pool & Spa.

9.4 out of 10, Exceptional, (23)
"We had a great a time! Would definitely stay again!"
The price is SAR 1,688
SAR 2,891 total
includes taxes & fees
18 Feb - 19 Feb
504 | Luxurious Beaver Creek, Ski in/out + Ski Valet, 4 Season Pool & Spa.

Stunning views from this 5 bedroom home on 8 acres, sleeps 12

9.8 out of 10, Exceptional, (127)
"A family trip with children, adult grandchildren, spouses. All were entertained with billiards ,foos ball, euchre, charades and a parade of trips to the hot tub, after vigorous skiing at Ajax and The highlands with a trek up to Highland a bowl in 26 min, for the fastest!! Well appt home, especially appreciated the ski lockers!Son in law a chef, so splendid meals at home ,and clean up a breeze with two dishwashers.Can’t say enough nice things about this home, kudos to the owners and the listing...
Stunning views from this 5 bedroom home on 8 acres, sleeps 12

Above it All - Highest rental house on the hill!

10.0 out of 10, Exceptional, (42)
"Wonderful Christmas in this beautiful snowglobe of a home!"
Above it All - Highest rental house on the hill!

10MM Aspen Residence -Walk to Town & Ski Slopes by GuaranteedRental

8.6 out of 10, Excellent, (4)
"The house is wonderful. Two master suites with steam showers really made our stay wonderful. Downstairs is perfect for a lot of kids with 4 bunks and pool table. We will definitely be reserving this house again "
10MM Aspen Residence -Walk to Town & Ski Slopes by GuaranteedRental

Carbondale Townhome with A/C, WiFi, and Backyard

9.8 out of 10, Exceptional, (45)
"We booked this condo for a family ski trip. The condo provides convenient access to all of the attractions and activities in the area, and we would not hesitate to book another stay here when we are back in the area."
Carbondale Townhome with A/C, WiFi, and Backyard

Downtown Glenwood Retreat

Downtown Glenwood Retreat

Pet-friendly 5 bed/4 bath home, just minutes to Beaver Creek, Avon, and Vail

9.4 out of 10, Exceptional, (32)
"We very much appreciated being able to bring our furry family members. Thank you!Good location between Beaver Creek and Vail. We had cars so it was fine not being convenient to any shuttle stops. It’s in a neighborhood so it was quiet and pleasant. Typical mountain condo otherwise. We had many meals in the condo (Christmas week) and it was well equipped for that. The place definitely has a lot of wear and tear on it and could use a refresh. Worked fine for us. Thanks!"
Pet-friendly 5 bed/4 bath home, just minutes to Beaver Creek, Avon, and Vail

Luxury Ski in Out, Walk to Ritz Carlton, Air conditioned, Private Hot Tub, Pool!

10.0 out of 10, Exceptional, (25)
"Property manager was always quick to respond. One minor issue with the property which was addressed immediately. House had plenty of room for two families with nine total people. We would stay here again."
Luxury Ski in Out, Walk to Ritz Carlton, Air conditioned, Private Hot Tub, Pool!

Gorgeous small apartment with everything you need!

10.0 out of 10, Exceptional, (115)
"Love this property. Quaint and cozy! Has everything you could possibly want. This has become a regular getaway for us! Thanks again for a great stay!"
Gorgeous small apartment with everything you need!

Incredible Views of Snow Covered Peaks - Hot Tub - Fire Ring - 5 Ski Mountains

10.0 out of 10, Exceptional, (115)
"It was beyond expectations with the house and the view and the wildlife there were mule deer in the yard every morning all day while we were in the hot tub and all we could see Elk in the further fields. It was nice to take a drive and find them if you are not an animal person the views were breathtaking The property was beautiful. We had fires inside and outside plenty of firewood, wanting for nothing town was close enough where it wasn’t an inconvenience, but the house was just far enough. You...
Incredible Views of Snow Covered Peaks - Hot Tub - Fire Ring - 5 Ski Mountains

Comfortable Mountain Home Near Downtown Glenwood & 15 mi. to Skiing!

9.4 out of 10, Exceptional, (30)
"Was a lovely place and provided everything we needed. lovely location and easy drive to the hot spring and downtown. If you plan to cook, make sure you get everything you need including spices and food storage. "
Comfortable Mountain Home Near Downtown Glenwood & 15 mi. to Skiing!

Private Hot tub/Fire Table on Large Deck overlooking Eagle River! Fly-fishing!

10.0 out of 10, Exceptional, (107)
"We love this house. Our family has stayed here several times. The location is wonderful. The house is perfect for our big family, very spacious and comfortable. So many things in this house make you feel like you are at home. Plenty of space for everyone. Kathy is a wonderful host and always responds immediately if needed. "
Private Hot tub/Fire Table on Large Deck overlooking Eagle River! Fly-fishing!

Be in the middle of it all in the cutest downtown Victorian THOROUGH SANITIZING

9.6 out of 10, Exceptional, (115)
"The location was good and we had most of the thing we needed. Our stay could have been more comfortable with more than one roll of toilet paper, a window covering on the front door, and a porch light. The hosts communication could have been improved by replying to these concerns. Host did try to provide a phone number and a website for local information, however, these were blanked out by Vrbo. "
Be in the middle of it all in the cutest downtown Victorian THOROUGH SANITIZING

Striking Home W/Hot Tub between Vail & Beaver Creek!

10.0 out of 10, Exceptional, (239)
"Our group loved our stay! We had a group of 7, including 4 adults and 3 teenage children. The location is great, about 10-15 minutes door-to-door for either Vail or Beaver Creek. The bus is near if you prefer that option. The location was nice, in a small residential area that was pretty quiet even while so close to skiing. The accommodations were very comfortable and place very clean. Host was very communicative and helpful. The hot tub is VERY nice after a cold day of skiing, as described, it...
Striking Home W/Hot Tub between Vail & Beaver Creek!

Modern Mountain Home in Glenwood Springs, CO

10.0 out of 10, Exceptional, (49)
"This place looks even better than the photos. Christine and Alex were extremely lovely. The location is great nice and quiet but not far at all from town. I will definitely be back again in the future!"
Modern Mountain Home in Glenwood Springs, CO
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other property types in Gypsum

The Gant

4.0 star property
9.6 out of 10, Exceptional, (849)
"Good location. Great room! Very helpful and friendly staff!"
The price is SAR 2,293
SAR 2,814 total
includes taxes & fees
26 Jan - 27 Jan
The Gant

Aspen Square Condominium Hotel

4.0 star property
9.6 out of 10, Exceptional, (840)
"Perfect location. We will return."
The price is SAR 2,848
SAR 3,515 total
includes taxes & fees
26 Jan - 27 Jan
Aspen Square Condominium Hotel

Beyul Retreat

3.0 star property
9.2 out of 10, Wonderful, (50)
"The staff were incredibly welcoming and helpful throughout our stay. I wish i could give them 100 stars. "
The price is SAR 652
SAR 777 total
includes taxes & fees
19 Jan - 20 Jan
Beyul Retreat
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.