Photo by mrstigger49

Search Vacation Homes in Gypsum

    calendar shield illustration
    Change your mind
    Book hotels with free cancellation
    deals illustration
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    bed illustration
    Be picky
    Search almost a million properties worldwide

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

Compare 1310 Vacation Homes in Gypsum with updated reviews, rates, and availability.

Mountain Retreat w/ Hot Tub, Scenic Decks, Grill, Dog Friendly & 7 mi. to Skiing

10.0 out of 10, Exceptional, (2)
"Clean, comfortable and quiet. Somewhat dated but overall highly recommended "
Mountain Retreat w/ Hot Tub, Scenic Decks, Grill, Dog Friendly & 7 mi. to Skiing

Quiet, pet friendly, enclosed yard, biking trails close by

9.8 out of 10, Exceptional, (276)
"Very wonderful stay perfect for our dog. "
Quiet, pet friendly, enclosed yard, biking trails close by

Tranquil Mountain Getaway

10.0 out of 10, Exceptional, (22)
"Great central location to all surrounding activities. Plenty of room for four teenager's and two adults. "
The price is AED 893
AED 1,684 total
includes taxes & fees
18 Jun - 19 Jun
Tranquil Mountain Getaway

Beautifully Appointed Victorian Home, in the Heart of Town, Walk to the Pool!

9.6 out of 10, Exceptional, (106)
"This home is in a perfect location to easily walk to restaurants, coffee shops, or the hot springs. Has a lovely living room and a den/office that is separate if someone in your party needs a little quiet spot. Lots of games as well. "
Beautifully Appointed Victorian Home, in the Heart of Town, Walk to the Pool!

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

9.6 out of 10, Exceptional, (117)
"Super cute little place right off the main part of town walking distance to everything. Truly lovely."
Be in the middle of it all in the cutest downtown Victorian THOROUGH SANITIZING

Modern Mountainside Home w/ Large Deck, Near Downtown & Skiing

9.6 out of 10, Exceptional, (35)
"House is very comfortable. Driveway is steep and prone to sliding in the snow."
Modern Mountainside Home w/ Large Deck, Near Downtown & Skiing

Family/Lrg Groups/King Bed/420/Hike/Bike/Ski/Raft/Firepit/Mountain Views

9.8 out of 10, Exceptional, (51)
"We had an absolute fabulous 3 day weekend. Bridget is incredible! The house is beautiful, spacious and comfy with a huge yard. We brought our dogs with us too and they loved the yard. Bridget was so amazing. She brought us fresh ground coffee for our stay, she packed the pantry with stuff for s’mores and even let our dogs out for a potty break while we were at the hot springs. She truly went above and beyond any other host we have ever stayed with. Thank you so much!! We will absolutely be back...
The price is AED 1,781
AED 2,526 total
includes taxes & fees
29 May - 30 May
Family/Lrg Groups/King Bed/420/Hike/Bike/Ski/Raft/Firepit/Mountain Views

Fully Renovated Victorian Home w/ Unbeatable Location, Dwntwn Core, Walk to Pool

9.6 out of 10, Exceptional, (27)
"Worked great for us!"
Fully Renovated Victorian Home w/ Unbeatable Location, Dwntwn Core, Walk to Pool

Historic Renovated Home Steps to dwtn & Hot Springs Pools, large deck, firepit

9.8 out of 10, Exceptional, (63)
"Great property, plenty of pillows and blankets, loved the big table for visiting with friends!"
Historic Renovated Home Steps to dwtn & Hot Springs Pools, large deck, firepit

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

10.0 out of 10, Exceptional, (122)
"Its a wonderful home for family and friens"
Incredible Views of Snow Covered Peaks - Hot Tub - Fire Ring - 5 Ski Mountains

Life is GRAND! So very GRAND!

9.6 out of 10, Exceptional, (18)
"We had a great time and Jenelle, the host, was exceptionally attentive. Awesome location, easy to get to the attractions."
Life is GRAND! So very GRAND!

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

9.8 out of 10, Exceptional, (131)
"We've stayed here 5 times now. It's been a great place for our group of 8-10 to have our annual ski trip. The listing says it all, and accurately."
Stunning views from this 5 bedroom home on 8 acres, sleeps 12

Locally owned family-friendly mountain getaway!

10.0 out of 10, Exceptional, (54)
"Beautiful house with plenty of space for gathering. Close to other family that lives in the area. "
Locally owned family-friendly mountain getaway!

Downtown Carbondale Duplex with Enclosed Yard, no cleaning fee

10.0 out of 10, Exceptional, (25)
"Super easy check in. Clean, comfortable and great location. I would definitely stay there again!!! "
Downtown Carbondale Duplex with Enclosed Yard, no cleaning fee

Newly Renovated Mtn Home w/ views, backyard oasis, 2 grills, near dwtn & Pools

9.8 out of 10, Exceptional, (76)
"Perfect for a quick getaway with friends"
Newly Renovated Mtn Home w/ views, backyard oasis, 2 grills, near dwtn & Pools

Cozy Mountain Retreat! Golf, Fish,Hot Tub, Pet Friendly, 30 miles to Aspen!

10.0 out of 10, Exceptional, (28)
"Great stay, host was great. "
The price is AED 1,282
AED 2,832 total
includes taxes & fees
8 Jun - 9 Jun
Cozy Mountain Retreat! Golf, Fish,Hot Tub, Pet Friendly, 30 miles to Aspen!

Stunning mountainside home with hot tub, fireplace & washer/dryer - dogs welcome

8.0 out of 10, Very Good, (13)
"House was nice, clean, and well-taken care of. We enjoyed our time there. "
The price is AED 694
AED 3,200 total
includes taxes & fees
29 May - 30 May
Stunning mountainside home with hot tub, fireplace & washer/dryer - dogs welcome

HOUSE 2 blocks from Hotel Colorado, WALK to restaurants & Hot Springs Pool!

HOUSE 2 blocks from Hotel Colorado, WALK to restaurants & Hot Springs Pool!

Charming Family Friendly Mountain Home, Minutes to Skiing & Downtown GWS!

9.8 out of 10, Exceptional, (28)
"Ryan is a great host!"
Charming Family Friendly Mountain Home, Minutes to Skiing & Downtown GWS!

Hillside Home w/ Views, Lounge Decks, Bbq, 5Min to Downtown & Hot Springs Pools!

9.6 out of 10, Exceptional, (44)
"We enjoyed Glenwood and soaking in the hot springs. The location was handy to all attractions."
Hillside Home w/ Views, Lounge Decks, Bbq, 5Min to Downtown & Hot Springs Pools!
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.
Save an average of 15% on thousands of hotels when you're signed in