
Vacation rentals with a pool in Wilmington
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Top-rated rentals with a pool in Wilmington
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Popular amenities for Wilmington rentals with a pool
House rentals with a pool

Outdoor Enthusiasts Paradise!
Our family had a beautiful, peaceful ski/snowboard vacation at Samantha’s home. The house was exceptionally clean and Samantha was an attentive host. We’ll hopefully visit again!

Adams Farm-"The Little Farmhouse"
We had an amazing stay! The house is lovely and very comfortable, perfect for going skiing at mount snow and cross country skiing and prospect mountain. We were really glad to have picked it. The house is spacious, we all had a lot of room to ourselves, and the kitchen had everything we needed. The farm is gorgeous. Great grocery stores nearby. Sharon was amazing - so helpful when a winter storm threatened to make it hard for us to drive home. She offered us extra time or even another night discounted, which was really generous. She also communicated with friends to help us determine if the road back to NYC had been cleared. We are so grateful for her help! We hope to return in warmer weather to enjoy the farm even more.

The Villa - Industrial Farmhouse with Hot Tub
We absolutely loved staying here- beautiful and laid out perfectly for 2 families, each with 2 little kids. Super convenient location to Mt. Snow. We look forward to staying here again!

The Brick House on Washington Street
We had a great stay in Keene. Ruth is a fantastic hostess. Her house is just close enough to Main Street to keep it a walkable distance to multiple restaurants and shopping. The house is a nice cozy spot that was big to accommodate my whole family meeting up for a fun winter weekend in Keene. I would stay there again without hesitation

Ski and tennis house by Stratton Ski Resort.
We spent our winter break at Adam's condo. This condo experience had all the important Cs: Clean Condo - it was very clean upon arrival. Convenient Condo - the Stratton shuttle stops right outside the door. Communicative Condo Owner - any questions we had were answered in a timely manner. Cost effective Condo - great value Okay I went overboard with the Cs but honestly it was such a great experience. Adam is great host and the condo worked out perfect for us! Hopefully we get a chance to stay here again!

Idyllic Dorset Home: Serene Escape w/amazing views
My group of 9 had a wonderful stay here! The house was very spacious, clean, and modern and accurately represented in the posting. John was extremely responsive during our process and proactively checked in with us to ensure we were able to check-in to the property smoothly. We had a small issue with one of the stove top burners and when we reached out to John, he followed up immediately to resolve the issue. I highly recommend staying here!

Luxury Mid-Century Modern Vermont Home, Okemo View
Wonderful Stay with Family – Highly Recommended! We had an amazing stay at this property with our family. The house was spacious, clean, and had all the amenities we needed for a comfortable stay. The host was fantastic – very responsive and always available to help with any questions we had. Communication was seamless, and he made sure we had everything we needed for a smooth experience. We really appreciated his hospitality. I highly recommend this place for anyone looking for a great place to stay. We had a memorable time and would definitely return!

Your country home awaits! Pool, tennis, Dogs loved
Great place to stay if you plan to ski or snowboard at Stratton. Close to the center of Manchester (grocery store, shops, etc . . .).
Condo rentals with a pool

Mount Snow Ski Chalet
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.

Renovated Condo - 5 min walk to Mount Snow
beautiful condo, well maitained and bathrooms new and remodeled. Great location to the ski lifts. He woks great, walls are solid because we couldn't hear the neighbors and all units were full this weekend. Nice fireplace and wifi worked great for the kids and all big flat screen tv's were excellent. Easy kitchen to cook in for the whole family. Best condo we've stayed at in Mt. Snow. Owners answered all our questions and recommendations

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

New - walk to Mt Snow w/ Tub & Gym
We loved the proximity to Mount snow, and the layout of the place was cozy and comfortable. We loved the newly renovated kitchen and all kitchen supplies were new. We didn’t get to use the amenities but we loved the sauna and hot tub offerings!

Stratton Duplex Condo Steps to Lifts, Village!
Great walkable location. Loft space granted nice privacy for 2 couples or extended family. Fireplace and living room were cozy.

Cozy Condo @ Jiminy Peak
We always book with Dawn! Her place is amazing. We feel right at home. She ensures the house has everything you could need in case you forget something. There are extra details to make your stay more comfortable. Her linens are softer than mine at home! There is plenty of space for my family of five to stay comfortably. I highly recommend booking here! We can’t wait until our next stay here.

Mt. Snow Condo with Pool-Hot Tubs-Sauna MTN Views
Had a lovely stay at Leah’s condo. Very comfy and cozy and super close to Mt Snow!

Premier Stratton Village Location - Pool & Hot Tub
Very lovely place, stayed for the last week of the season but definitely worth the stay! The garage parking was a bit tricky to find at first but it is directly across the welcome center, sad I didn't bring a bathing suit for the jacuzzi!
Quick stats about vacation rentals with a pool in Wilmington
Total rentals
80 properties
Nightly prices starting at
$110 before taxes and fees
Total number of reviews
2.6K reviews
Family-friendly rentals
60 properties are a good fit for families
Pet-friendly rentals
20 properties allow pets
Rentals with dedicated workspaces
40 properties have a dedicated workspace
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- Okemo Mountain Resort
- Jiminy Peak Mountain Resort
- Stratton Mountain Resort
- Magic Mountain Ski Resort
- Saratoga Spa State Park
- Albany Center Gallery
- Monadnock State Park
- Berkshire East Mountain Resort
- Saratoga Race Course
- Mount Sugarloaf State Reservation
- Mount Greylock Ski Club
- Bousquet Mountain Ski Area
- Mount Snow Ski Resort
- Otis Ridge
- Norman Rockwell Museum
- Naumkeag
- Hooper Golf Course
- National Museum of Racing and Hall of Fame
- Peebles Island State Park
- Northern Cross Vineyard
- Pineridge Cross Country Ski Area
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- Willard Mountain
- Hancock Shaker Village
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