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 Wardsboro
5 out of 5 average rating, 59 reviews

Hot Tub, Game Room, Minutes to Mt. Snow & Stratton

DanielRating, 5 stars1 week ago
We had a great vacation at Whitley’s Airbnb. The house was very clean, spacious, and provided lots to do. It was also great being so close to Mt. Snow. I highly recommend this house and would love to come back!
Guest favorite
Home in Dover
5 out of 5 average rating, 15 reviews

Private chalet tucked in the green mountains

CarolineRating, 5 stars1 month ago
We had a wonderful weekend at Liz’s cabin. Everything was clean. Hot tub was awesome. Would recommend to anyone looking for a beautiful cabin getaway.
Guest favorite
Home in Wilmington
5 out of 5 average rating, 10 reviews

Modern 4BR Cabin, Near Lake & Mt. Snow

OmarRating, 5 stars5 months ago
Host is extremely responsive, friendly, and accommodating. The house is well equipped with many kitchen supplies, including spices and other cooking products. The home is cozy and host equipped home with necessary items needed for a stay in the winter, such as sufficient salt, sand, shovels, and flashlight. the amenities of the chimney hill clubhouse are very family friendly as well. These include an indoor pool, hot tub, ping-pong, table, arcade, and indoor movie theater. Overall, a lovely home for a family and fantastic host.
Top guest favorite
Home in Wilmington
4.96 out of 5 average rating, 28 reviews

Family/Dog Friendly Mountain Home w/ Amenities

LouisRating, 5 stars4 days ago
Jake’s home is outstanding. The beds are very comfortable. The internet is good, The home has lots of space , a great kitchen with all amenities that we needed. Gas stove etc. The outlay was very comfortable and made for the perfect vacation. I’ve stayed at many homes in the area, Jake’s place is by far the best. We also went to the Clubhouse and used the pool and hot tub which was an added surprise.
Guest favorite
Home in Wilmington
5 out of 5 average rating, 12 reviews

4bed, 2bath @ Chimney Hill w/Hot Tub & EV Charger

YoniRating, 5 stars3 months ago
Lovely home. Hopefully I can stay here next year.
Top guest favorite
Home in Salem
5 out of 5 average rating, 14 reviews

The Lodge, a 70's Getaway w/swimming pool

AyeshaRating, 5 stars5 months ago
If you are reading this review.. BOOK this place right now. I have stayed in over 50 AirBnB’s across the US and this one stands out on another level. The attention to detail in every corner. The cleanliness. The amazing hospitality with the host walking us around the entire place giving us a tour. All the games blankets full bar and kitchen utensils were an amazing touch. I would easily go back. Loved this cabin so much it was home away from home. Did a small friend’s gathering for New Year’s Eve we spent 4 days here and didn’t want to leave. I’m telling you, if you see this review just book it. There isn’t a better option.
Guest favorite
Home in Wilmington
5 out of 5 average rating, 16 reviews

Stylish Chimney Hill Home - Close to Mt. Snow!

SetarehRating, 5 stars3 months ago
No complaints. This is a beautiful home that had everything we needed for our weekend ski trip with 4 adults and 1 toddler. Very clean, cozy and a great location close to Mt. Snow. We really enjoyed our stay, thank you!
Top guest favorite
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!!

Condo rentals with a pool

Guest favorite
Condo in Stratton
4.97 out of 5 average rating, 65 reviews

Stratton Mt Summer: Golf, tennis, hike, bike, swim

NicoleRating, 5 stars3 months ago
Perfect location just steps from Stratton Village! The room was very clean and we loved the outdoor hot tubs and complimentary Starbucks coffee in the morning. Luke was a great host, very responsive and even offered us a later checkout. Would definitely stay again!
Guest favorite
Condo in Peru
4.97 out of 5 average rating, 89 reviews

Cozy Mountain Condo - Let's Hike!

StevenRating, 5 stars3 months ago
Laura's place was great. It was clean, right on Bromley Mountain (ski on and ski off), and a quick drive to Manchester. Laura was very responsive and helpful. Even sent me a youtube video to help with my technical challenges of working with two remotes for the Smart TV. I highly recommend this AIRBNB.
Guest favorite
Condo 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.
Superhost
Condo in Dover
5 out of 5 average rating, 11 reviews

Cozy Updated 2 Bedroom Corner Condo

NicoleRating, 5 stars28 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!
Guest favorite
Condo in Stratton Mountain
4.88 out of 5 average rating, 8 reviews

3BR/3BA Hearthstone condo with pool access

Jennifer CatherineRating, 5 stars3 months ago
Great location in Stratton Village . The condo was perfect and had everything we needed .
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 stars2 months 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
4.95 out of 5 average rating, 63 reviews

Renovated Stratton Mtn Studio | Walk to Lifts

MelissaRating, 5 stars1 month ago
Very well maintained, beautiful condo at base of Stratton Mountain. Host provided excellent, detailed communications.
Guest favorite
Condo 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!

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