Bennington County Vacation Rentals with Pools
750 ft²
4 Guests
1 Bedroom
1 Bathroom
Family Friendly
Condo
- Skiing
- Fireplace/Heating
- Pool
US $205/Night
For 7 Nights US $1,437
1001.04 ft²
8 Guests
3 Bedrooms
2 Bathrooms
Free Cancellation
House
- Skiing
- Fireplace/Heating
- Pool
US $449/Night
For 7 Nights US $3,145
1 Bedroom
1 Bathroom
Family Friendly
Bed & Breakfast
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $182/Night
For 7 Nights US $1,271
6 Guests
2 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $525/Night
For 7 Nights US $3,675
241.59 ft²
44 Guests
18 Bedrooms
18 Bathrooms
Ocean View
Bed & Breakfast
- Oceanfront
- Skiing
- Fireplace/Heating
US $185/Night
For 7 Nights US $1,295
1000 ft²
4 Guests
2 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $271/Night
For 7 Nights US $1,896
365.97 ft²
6 Guests
8 Bedrooms
2 Bathrooms
Ocean View
Cabin
- Oceanfront
- Skiing
- Fireplace/Heating
US $196/Night
For 7 Nights US $1,374
6 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Condo
- Hot Tub
- Fireplace/Heating
- Pool
US $479/Night
For 7 Nights US $3,351
243.98 ft²
14 Guests
21 Bedrooms
4 Bathrooms
Bed & Breakfast
- Skiing
- Fireplace/Heating
- Pool
US $175/Night
For 7 Nights US $1,225
4 Guests
1 Bedroom
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $335/Night
For 7 Nights US $2,343
208.1 ft²
10 Guests
24 Bedrooms
4 Bathrooms
Bed & Breakfast
- Oceanfront
- Skiing
- Fireplace/Heating
US $181/Night
For 7 Nights US $1,267
900 ft²
6 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $219/Night
For 7 Nights US $1,530
Why Choose Rent By Owner for your Bennington County Vacation Rentals with Pools?
What makes our Vacation Rentals with Pools special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Weekly Weather Forecast for Bennington County
How to Book Your Bennington County Vacation Rentals with Pools
What's our booking process?
Our platform allows you to browse a curated selection of vacation rentals with pools. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Explore and book the perfect rental in Bennington County
Common Vacation Rentals with Pools Amenities
What amenities can you expect?
Our Vacation Rentals with Pools are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Other Places to Stay in Bennington County, VT
Bennington
Manchester
Bondville
Manchester Center
Londonderry
Sunderland
Arlington
Dorset
Bromley Mountain
Bromley Mountain Ski Resort
Winhall
Bennington County Vacation Rentals with Pools Frequently Asked Questions
1. What are the top Rentals With Pools in Bennington County?
There are a lot of options in Bennington County. If you plan on staying in the Bennington County area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Rentals With Pools in Bennington County:
- Amazing Vermont Estate with 2 houses, 11 bedrooms, a pool, sauna, and gameroom!
- Beautiful Mountain Getaway - Last Minute Booking Promos! Minutes from Manchester
- Beautiful Lakeview Log Cabin on 60-Acre Property
- Sleep 34: 15 bedrm/12 bath Mansion! Ski Weddings Reunions Yoga Corporate - Dogs!
- Located At Bromley Mountain
- Picture Perfect Vermont log cabin - close to everything Manchester has to offer
- Cozy Country Cabin Vermont
- Winterbrook House: A Jewel in Manchester Village. 15 min to Skiing & Equestrian
- Seesaw's Lodge
- 4 Bedroom Mountainside Condo - Enjoy Beautiful Vermont This Winter!
2. How many Rentals With Pools are available in Bennington County?
Currently, the total number of properties listed by RBO in 2026 is over 245 in the Bennington County area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Rentals With Pools in Bennington County.
More Rentals You May Like Near Bennington County
10 Guests
4 Bedrooms
3 Bathrooms
Free Cancellation
House
- Fireplace/Heating
- Pool
- Pet Friendly
US $499/Night
For 7 Nights US $3,493
2100 ft²
8 Guests
3 Bedrooms
1 Bathroom
Family Friendly
House
- Private Pool
- Hot Tub
- Fireplace/Heating
US $263/Night
For 7 Nights US $1,842
4 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $322/Night
For 7 Nights US $2,252
1000 ft²
6 Guests
2 Bedrooms
1 Bathroom
Ocean View
Apartment
- Private Pool
- Hot Tub
- Fireplace/Heating
US $223/Night
For 7 Nights US $1,561
958 ft²
6 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Condo
- Skiing
- Fireplace/Heating
- Pool
US $275/Night
For 7 Nights US $1,928
400 ft²
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Condo
- Pool
- Balcony/Terrace
- Pet Friendly
US $217/Night
For 7 Nights US $1,517
1100 ft²
6 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Condo
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $773/Night
For 7 Nights US $5,413
850 ft²
4 Guests
1 Bedroom
1 Bathroom
Family Friendly
Condo
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $632/Night
For 7 Nights US $4,427
750 ft²
5 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Condo
- Pool
- Pet Friendly
- Kitchen
US $344/Night
For 7 Nights US $2,410
500 ft²
3 Guests
1 Bedroom
1 Bathroom
Family Friendly
Condo
- Pool
- Balcony/Terrace
- Pet Friendly
US $299/Night
For 7 Nights US $2,094
400 ft²
4 Guests
1 Bedroom
1 Bathroom
Family Friendly
Condo
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $280/Night
For 7 Nights US $1,963
325 ft²
1 Guest
1 Bedroom
1 Bathroom
Family Friendly
Bed & Breakfast
- Hot Tub
- Fireplace/Heating
- Pool
US $265/Night
For 7 Nights US $1,854
