Holiday rentals with a pool in Stratton

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Popular amenities for Stratton rentals with a pool

House rentals with a pool

Guest favourite
Home in Salem
4.98 out of 5 average rating, 192 reviews

Magical Farm Getaway - a must visit!

BriannaRating, 5 stars2 weeks ago
We had a wonderful & relaxing weekend here with a large group for my sister's lowkey bachelorette party. Even with a day of non-stop pouring rain, we were perfectly content with staying in and enjoying the coziness of the house. We had a blast watching the chickens roam around and hanging out with the overly-friendly barn cats while we sat outside. The goats & pigs were happy to greet us at the fence every time. The hot tub and pool were perfect! Highly recommend staying here if you're looking for a beautifully scenic and peaceful getaway. Thanks, Sarah & BBVF team!
Guest favourite
Home in Colrain
4.9 out of 5 average rating, 129 reviews

The 1770 House

CatherineRating, 5 stars1 month ago
Historic house on a beautiful property. Kitchen had all the equipment you could need along with top of the line stove and oven. Make cooking for a large group easy and enjoyable!
Top guest favourite
Home in Wardsboro
5 out of 5 average rating, 12 reviews

MtSnow/Stratton Ski Lodge-Hot Tub-Game Room-Pool

ChrisRating, 5 stars3 months ago
This home is Stunning!!! In every aspect! Every room is beautiful and Michelle has thought of every detail to make you feel at home. Incredibly comfortable beds and linens, a fully stocked kitchen for all your cooking/takeout desires, and hang out spot for the kids with air hockey and arcade basketball! I could go on and on. You will not want to leave!
Guest favourite
Home in Keene
4.93 out of 5 average rating, 211 reviews

The Brick House on Washington Street

PaulRating, 5 stars2 weeks ago
Great stay and was exactly what we needed for our entire family for a weekend wedding!
Guest favourite
Home in Plainfield
4.89 out of 5 average rating, 139 reviews

Historic Home on 17 acres of land. Go escape!

BrandieRating, 5 stars3 months ago
Staying here is always a joy for the entire family! It has become an annual tradition that we all look forward to in winter. Thank you for being so accommodating with our schedule and a special thanks to Mitchell for going the extra mile to snow blow a waking path for me and the dogs to keep our daily routine of visiting the horses, after the last storm brought over 13” of snow. P.S. the new stove/oven is amazing!! 🤩
Top guest favourite
Home in Dover
4.98 out of 5 average rating, 52 reviews

Spring Getaway @ Mt Snow! Hike, Bike, Sleeps 8.

JessicaRating, 5 stars3 months ago
We had such a great time staying here! The house was so cozy and clean and was perfect! Felt like being at home and not staying in an Airbnb. Super close to the mountain, especially if you park in carinthia! Loved the guest book that they have in the kitchen, a fun added touch! Robert was extremely responsive to any messages and super accommodating with us and our needs! Absolutely would recommend staying here!!
Guest favourite
Home in Granville
4.93 out of 5 average rating, 106 reviews

Historic 1850’s Renovated Farmhouse w/ Pool!

KimberlyRating, 5 stars3 weeks ago
9 adults and 3 children all met up for a family weekend! We came from NY, NH and Maine! The house was perfect! Plenty of room to gather or separate! Even tho it was a chilly rainy weekend the kids managed to get in plenty of pool time! Tanya was very responsive and Melvin was the greatest! Our first morning he came right over to fix a slow drain. Highly recommend!! Kim and family
Guest favourite
Home in Williamstown
4.89 out of 5 average rating, 218 reviews

Hollywood Bungalow in the Berkshires #C0191633410

JohnRating, 5 stars4 months ago
We had a great stay at the Hollywood Bungalow. House was described accurately and had so many thoughtful touches to make us feel welcome. Diana met us upon arrival and walked us around the property and the house. Such a great host! She had generously provided snacks, treats and gave a thorough overview for our stay. We were primarily focused on skiing at Jiminy Peak which was a short 20 minute drive. We also brought our 5 year-old rescue who had the best vacation of her life. She was able to use the fenced-in backyard to run around off leash and even meet a new friend when Jackson's dog visited. Diana even shoveled walking paths in the yard throughout our stay so we could get around in the high snow. The Screening Room is awesome and provided hours of entertainment. Quiet street and picturesque location. We will definitely return.

Apartment rentals with a pool

Guest favourite
Apartment in Dover
4.83 out of 5 average rating, 108 reviews

Mount Snow Ski Chalet

BarryRating, 5 stars3 months ago
Great place to stay. There are no Ubers the week we stayed there and we should have rented a car. But the place was great.
Guest favourite
Apartment in Dover
5 out of 5 average rating, 18 reviews

Slopes N Seasons | Trailside Condo at Mount Snow

JosephRating, 5 starstoday
Outstanding stay at Erin’s beautiful place. Immaculately clean. Perfectly remodeled with all high end fixtures and decorations. Plenty of accommodations in the condo. Very quiet in the summer. Facilities are top notch with indoor and outdoor pool. Grill and fire pit in the common area that you can reserve as well as gorgeous common area with games activities and a nice gym. Walk or ski to mount snow Sundance area. Can’t say enough and can’t wait to return. Thankyou for hosting.
Guest favourite
Apartment in Dover
4.91 out of 5 average rating, 110 reviews

Seasons on Mt Snow Condo - Ski/Hike/Bike/Swim

MichaelRating, 5 stars3 months ago
We stayed at Julia's vacation rental for a 3-day weekend with our four children under the age of 12. The things that were great: 1) the unit is 150 foot walk in ski boots from a ski trail that will take you to the Mount Snow lift, which was great because we didn't have to shlep 4 kids ski gear, 2) the four kids loved the bunk bed room and were comfortable, 3) there are two large shelves of board games the kids enjoyed, 4) the access to the Sports Center which has a heated indoor pool and hot tubs were a great way to end the day after skiing, 5) the outdoor locker was a great place to dump all the ski gear (much better storage location than inside the car or inside the unit) and 6) very nice fluffy towels and bed sheeting was comfortable. A combined liquid shampoo and body soap is provided in each bathroom, which is the same that we use to bath our kids at home.
Guest favourite
Apartment in Dover
4.87 out of 5 average rating, 239 reviews

Mt Snow Ski In/Out at Seasons

MarkRating, 5 stars2 months ago
The unit is very comfortable for a family and very convenient to Mount Snow. Updated bathrooms and washer/dryer. Great clubhouse and pool facilities at Seasons condo. Andrew was a pleasure to work with.
Guest favourite
Apartment in Stratton
5 out of 5 average rating, 11 reviews

Luxurious Mountain Escape at Stratton

RachelRating, 5 stars3 months ago
This was a perfect place to stay for two families (each with one infant), super short walk to the village plus getting in and out was a breeze with the garage in the building. Lots of space plus the hot tub and pool - will definitely come back again!
Guest favourite
Apartment in Ludlow
4.93 out of 5 average rating, 110 reviews

One Bedroom Suite Near Okemo

ChristopherRating, 5 stars2 months ago
Excellent apartment in a resort hotel. Well staffed and the property is kept in excellent condition. Highly recommend this host.
Top guest favourite
Apartment in Dover
5 out of 5 average rating, 58 reviews

Four Seasons Slope-side Getaway at Mount Snow

AlexRating, 5 stars3 months ago
Dean and Tina are excellent hosts! We had a great weekend on the mountain. Their home is very comfortable and awesome location.
Top guest favourite
Apartment in Stratton
5 out of 5 average rating, 44 reviews

Your Vermondo awaits: Steps to Lifts & Village.

ErinRating, 5 stars2 months ago
We really enjoyed our stay here with our 3 kids! The second bedroom was perfect with the trundle and the bunk beds. The condo was well maintained and exactly as described. The heated pool and hot tubs were great after a day on the slopes. We enjoyed the close walk to the lifts at Stratton as well as the walk to the village. Would highly recommend!

Quick stats about holiday rentals with a pool in Stratton

  • Total rentals

    50 properties

  • Nightly prices starting at

    $77 SGD before taxes and fees

  • Total number of reviews

    1.3K reviews

  • Family-friendly rentals

    40 properties are a good fit for families

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wifi availability

    50 properties include access to wifi

Destinations to explore

  1. Airbnb
  2. United States
  3. Vermont
  4. Windham County
  5. Stratton
  6. Rentals with pools