Vacation rentals with a pool in Bennington County

Find and book unique homes with a pool on Airbnb

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Popular amenities for Bennington County rentals with a pool

House rentals with a pool

Top guest favorite
Home in Cambridge
4.97 out of 5 average rating, 39 reviews

Country hideaway

GwenRating, 5 stars8 months ago
Second visit and it was just as nice as the first. We like this house inside and out. The pool and walking trail through the woods are great, and the living room is super comfy for family hanging out at night or on a rainy morning. Highly recommend!
Guest favorite
Home in Dover
5 out of 5 average rating, 13 reviews

Hot tub | Shuttle | Ski back home!

B.B.Rating, 5 stars1 month ago
Four of us have stayed in 25 Vermont airbnb type places for ski trips in the last 35 years and this is one of the 5 best. The huge living room (comfortable even up to 8), the wood-burning fireplace, and the hot tub are the extra special features of the house. The backyard is very private and peaceful in case you plan to visit in the summer. There is a hawk nest within view of the hottub. Saying the kitchen is stocked with utensils is an understatement. We will return.
Guest favorite
Home in Wilmington
5 out of 5 average rating, 11 reviews

Outdoor Enthusiasts Paradise!

EmilyRating, 5 stars3 months ago
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!
Superhost
Home in Wilmington
4.87 out of 5 average rating, 171 reviews

Adams Farm-"The Little Farmhouse"

Catherine (Lou)Rating, 5 stars2 months ago
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.
Guest favorite
Home in Jamaica
4.96 out of 5 average rating, 25 reviews

Ski and tennis house by Stratton Ski Resort.

BillyRating, 5 stars2 months ago
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!
Guest favorite
Home in Dorset
4.95 out of 5 average rating, 22 reviews

Idyllic Dorset Home: Serene Escape w/amazing views

StacyRating, 5 stars2 months ago
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!
Superhost
Home in Dover
4.89 out of 5 average rating, 47 reviews

Queen Suite, Living Room, 2 TVs -Spring House 2

ElizabethRating, 5 stars21 months ago
My grandson and I stayed in the upstairs cottage next to the pool. The cottage itself was well equipped. My grandson is a picky eater, so we did virtually all our meals in the cottage by means of a fridge, mini freezer and microwave. We ate out twice in nearby restaurants. The grounds of FRE are beautiful and very well maintained. There are nice walks and hikes, if you are inclined. The staff is friendly and receptive. We enjoyed the pool all but 2 days because of the weather. The outside temps were mild, the pool temp very comfortable. The nearby town of Wilmington is cute, has many shops, restaurants and a few ice cream shops we tried. We happened upon their Blueberry Festival our last day with music, food, (blueberry) drinks and face painting. A very enjoyable Vermont experience all around.
Superhost
Home in Wilmington
4.87 out of 5 average rating, 23 reviews

Large Home - Close to Mt. Snow -Wilmington,VT

EricRating, 5 stars2 months ago
We had a family get together and we very much enjoyed our stay. It was great for the kids who had lots of space to play and access to the Clubhouse with the pool and game room was great. We were able to take advantage of Mt. Snow which was only 15 minutes away. Sharon was super responsive to all our questions and accommodating to us. We had a great time

Condo rentals with a pool

Guest favorite
Condo in Dover
4.83 out of 5 average rating, 108 reviews

Mount Snow Ski Chalet

BarryRating, 5 stars2 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.
Superhost
Condo in Dover
5 out of 5 average rating, 11 reviews

Cozy Updated 2 Bedroom Corner Condo

NicoleRating, 5 stars27 months ago
Greg has to be the most responsive, accommodating host I've ever had the pleasure of renting from. He gave me clear instructions, responded the minute I sent a question, and was very generous regarding check in and check out. What a great guy! The condo itself is in a great location. We didn't use the Moover but the stop is right outside the building's door. Like many ski condos it's basic but cozy. The neighbors were really audible in the bedroom, but we may have just had a weekend with some loud people next door! The best part (besides how great Greg was) is the view. It's so lovely to look out over the ski mountain. Overall a great value and a wonderful host. Thanks, Greg!
Superhost
Condo in Dover
4.92 out of 5 average rating, 12 reviews

Renovated Condo - 5 min walk to Mount Snow

Christoph GRating, 5 stars1 month ago
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
Guest favorite
Condo in Dover
4.91 out of 5 average rating, 110 reviews

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

MichaelRating, 5 stars1 month 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 favorite
Condo in Dover
5 out of 5 average rating, 17 reviews

'Bear Paw Lodge' w/Hot Tub* at BASE of Mt Snow

JoelRating, 5 stars1 month ago
My family of four had plenty of space for a relaxing weekend. Weather did not permit skiing but Mt Snow was right next door and Okemo ~60 mins away. Nice amenities in a great location.
Guest favorite
Condo in Stratton
4.94 out of 5 average rating, 33 reviews

Perfect 3 Br. Getaway Condo in Stratton, Vermont!

CarolineRating, 5 stars1 month ago
Lina was so responsive and helpful. Location could not have been more perfect. Such a lovely find! Thank you, Lina!
Guest favorite
Condo in Stratton
4.93 out of 5 average rating, 15 reviews

Stratton two bedroom condo on a shuttle

DrewRating, 5 stars1 month ago
Megan’s place was great for a weekend of skiing at Stratton. Right on a shuttle route that picks you up at the front door and is very reliable. Clean and comfortable. Megan was extremely helpful and responsive throughout the whole process from booking to check in and check out.
Guest favorite
Condo in Dover
5 out of 5 average rating, 23 reviews

Lyon Family Lodge - Ski-in/ski-out

BethRating, 5 stars4 months ago
Great location, ski on ski off and very nice community not far from restaurants. Jared was very responsive and flexible with check in time. Overall a great condo on the mountain and would stay here again.

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