Vacation rentals with a pool in Brattleboro

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Popular amenities for Brattleboro rentals with a pool

House rentals with a pool

Guest favorite
Home in Salem
4.98 out of 5 average rating, 191 reviews

Magical Farm Getaway - a must visit!

StephanieRating, 5 stars3 months ago
A fun winter break/birthday getaway! Sarah’s house had plenty of bedrooms for all guests. The game room, pool table, and wood stove/fireplace were great to have on these cold February days. Everyone enjoyed the sunroom and large dining table. The hot tub and outdoor sleds were used as well. The history of the house and beautiful views from the property were an interest to all. I bet this house is a lovely spot in the summer as well!
Guest favorite
Home in Greendale
4.96 out of 5 average rating, 100 reviews

Courtyard Garden | Pool | BBQ+Fire Tbl | Fireplace

RobertRating, 5 stars2 weeks ago
It's a shame I can't give 6 stars. Tania and Glenn anticipated every need for us - it was like a home away from home. We traveled for a family event and stayed for 5 days. The whole house had a tranquil, but hip, vibe. We were able to come into a prepped kitchen, and also grill out on this amazing patio with an immaculate garden. The house was so quiet that we all slept late every day. As hosts, Tania and Glenn went above and beyond. Not only did they prep us with area recommendations before we arrived, but checked in with us to make sure the stay was going well, and were so easy to work with as some plans changed mid-trip. Moreover, the house was completely prepped, with organized and easy-to-understand instructions for everything. All told, I felt more like family than an AirBNB renter.
Guest favorite
Home in Newfane
4.92 out of 5 average rating, 49 reviews

6 BR Perfect Private Retreat in Vermont!

AlexRating, 5 stars10 months ago
Large house in a very remote area. Approximately 70 acres. It was very relaxing and was nice to enjoy the pool which was professionally cleaned before arrival. The master bath has an incredible view of the mountains and an enormous shower. Pool table was fun and well taken care of. We stayed on probably one of the hotter weekends and the house cooled down at night pretty well just by opening the windows. Most rooms had ceiling fans if no other fans were provided. I can imagine this house would be amazing in the winter or fall too. With the screened in fireplace room and additional fire place inside the main house. You’re also close to 2 ski mountains each about 18 miles away. I could see myself renting again in the future. Thanks again
Guest favorite
Home in New Lebanon
4.98 out of 5 average rating, 59 reviews

Berkshire Mountain home views, pool, Queechy Lake

GeorgeRating, 5 stars3 months ago
The house was very spacious, the kids ranging from 6-10 loved the games, especially cue ball and fuzz ball. The adults loved the fact there was a lower half where the kids can watch movies and play, while the adults did grown up chatting in the living space. A memorable ski weekend that everyone enjoyed to the fulliest and sad it went so fast. We look forward returning one day in the spring or summer to see a different aspect of the area. Thank you!
Superhost
Home in Lee
4.87 out of 5 average rating, 30 reviews

* Private Berkshire Escape* Monthly Pricing Avail

JoanRating, 5 stars10 months ago
This gem of a house served as home base for my family of 4 when visiting Tanglewood & Berkshires area for a long weekend! The house is artfully decorated, with unique treasures we enjoyed exploring, common spaces for us to hang together as a family plus plenty of room for us to spread out for privacy. We especially enjoyed having the pool onsite, backyard fire pit, and multiple outdoor seating areas. Teva was a very responsive, helpful host! Went above and beyond! Thanks for an excellent stay!
Top guest favorite
Home in Pittsfield
4.98 out of 5 average rating, 56 reviews

Berkshire Lakefront Home W/Pool-100%Renovated

Lesley-AnneRating, 5 stars1 week ago
Our group of 10 family members and close friends had a wonderful time at this lovely house. It's large, clean, comfortable, and well equipped for cooking and relaxing together. The instructions were clear and comprehensive. Jay is friendly, knowledgeable, and responsive - in short, an excellent host. Our whole experience gets a big thumbs up!
Guest favorite
Home in Hartland
5 out of 5 average rating, 10 reviews

Private Farmhouse with in ground pool!

ChrisRating, 5 stars9 months ago
My family and I truly enjoyed our time spent at the farmhouse. Everything was as expected from the listing. The pictures do not do justice for the property. It's beautiful and well maintained. The pool was nice, warm, and clean. There are yard games readily available and a nice fire pit area. Brin and Maria are super responsive and left very detailed instructions on the property for you. Everything you need is there minus food, which is a 12-minute drive towards a few different grocery stores. The hill is so fun to roll down, too! Thank you so much!
Guest favorite
Home in East Chatham
4.92 out of 5 average rating, 25 reviews

10 Acre Country Estate with Pool, Hot Tub & Views!

SaraRating, 5 stars1 week ago
We had a great time during our stay! It was raining and cold, so while we couldn’t enjoy the pool, the hot tub was wonderful! The house was clean, spacious, and comfortable, which allowed our families to relax and enjoy the beautiful location!

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 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 favorite
Condo in Dover
4.91 out of 5 average rating, 110 reviews

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

MichaelRating, 5 stars2 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 favorite
Condo in Killington
4.95 out of 5 average rating, 105 reviews

⭐️Cozy Ski On/Ski Off 2-Bed/Bath w/Fireplace

PatriciaRating, 5 stars2 months ago
This space was perfect for our family. With walking distance to the entrance of the slopes, this location was ideal for our ski getaway. I appreciated the small touches that made this experience feel luxurious, the provided coffee, wine, wood for the usable fire place. The beds were comfortable and the space was spacious. We would definitely visit Jim’s place again!
Guest favorite
Condo in Dover
4.87 out of 5 average rating, 239 reviews

Mt Snow Ski In/Out at Seasons

MarkRating, 5 stars1 month 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 favorite
Condo in Dover
4.96 out of 5 average rating, 45 reviews

Ski in/out - 2BR Condo - Indoor Pool/Spa

DanielleRating, 5 stars3 months ago
Great condo at Mt Snow. Very clean and organized. Location is on the mountain. It requires some steep walking for ski in/ski out so keep in mind for younger kids while also carrying their gear. My kids are older so it wasn’t an issue for us but worth mentioning. Eric is the perfect host - always reachable and responsive. Super accommodating when he’s able to be. We got unlucky wind hold weather and he offered to extend our check out if we wanted to ski an extra day to make up for it. Truly awesome. Can’t go wrong.
Guest favorite
Condo in Stratton
4.98 out of 5 average rating, 46 reviews

A Village location, Steps to the Lifts & Village

LelahRating, 5 stars2 months ago
We loved staying at this property. The location is excellent for access to the village and the lifts. It is also cute to look out over the ice skating pond. It was clean, had all the kitchen amenities you would need to make food, and had fun ski-oriented decorations. It is also close to the hot tub and lounge area within the main building. It had everything we needed to make out ski weekend comfortable and memorable. Can't wait to stay again!
Guest favorite
Condo in Stratton
4.95 out of 5 average rating, 147 reviews

Cozy condo within walking distance to the slopes.

MaraRating, 5 stars2 months ago
You really can’t beat this location. It’s across the steet from the lifts and the village with lots of restaurants/bars/stores. The space was perfect for our family of four. Our two young children stayed on the pullout and we thought the king bed was quite comfy. We would def stay here again!
Guest favorite
Condo in Stratton
4.9 out of 5 average rating, 20 reviews

Stratton Duplex Condo Steps to Lifts, Village!

NathalieRating, 5 stars2 months ago
Great walkable location. Loft space granted nice privacy for 2 couples or extended family. Fireplace and living room were cozy.

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