
Vacation rentals with a pool in Bridgehampton
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Top-rated rentals with a pool in Bridgehampton
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

Southampton Charmer, 5 bedrooms w pool - Location
This 5-bedroom home boasts en-suite baths and elegant furnishings. The gourmet kitchen features marble countertops and stainless steel appliances, leading to a dining area. The lower level includes a spacious seating area and a game room with toys. The second floor houses a master suite with stunning views and three additional en-suite bedrooms. Located minutes from the village center, with restaurants, shops, and beaches nearby. A heated pool invites you to relax and enjoy the comfort of home.

Modern East Hampton Home w/ Heated Saltwater Pool
Peace and serenity in East Hampton and minutes from the Village. This exquisite modern home features high-end finishes such as Sub-Zero and Wolf appliances, quartzite waterfall kitchen island and counters, marble tiled bathrooms, designer mid-century decor and separately zoned air conditioning. The heated saltwater pool is surrounded by a bluestone patio, Ipe deck and huge yard. The house also features two wood-burning fireplaces in the living room and den and an outdoor fire-pit. RR# 24-656

Explore the Water & Woods at a Relaxing Retreat
Flick through records under soaring ceilings and hang out in the year-round hot tub at this East Hampton open-plan retreat. Unwind in the wooded backyard, take a dip in the pool or spa, detox in the sauna, grill on BBQ, relax in the movie-theatre seats to watch a film, then snuggle up to fireplace or firepit before drifting to sleep in super comfy beds. Minutes to village, beaches and hiking trails. Terrific for families & friends looking for a relaxing getaway. (No AI used in these photos!)

Hamptons Dream Suite
Hampton's Dream Suite- Is a guest suite in East Hampton, NY. From relaxing by the pool, to taking a day trip to Montauk, or visiting some of the best beaches in the Hamptons, the opportunities here are endless! It offers a bedroom with a Queen size Select Comfort bed, living room has two queen sofa beds and a full bathroom. It has a Kitchenette, Central AC/Heat with a 65" smart TV with surround sound and DVD, Blue ray and Xbox Games . There is also at TV and blue Ray player in the bedroom.

Modern farmhouse w/ pool, beach, horses and winery
A new, modernized farmhouse with a heated saltwater pool in the heart of North Fork. Nestled on an acre of lush, fully fenced yard, the home can easily accommodate up to 8 guests and all pets! Minutes away from Love Lane (Mattituck's charming downtown), Breakwater Beach (one of best beaches in North Fork), Mattituck train station and surrounding the award winning Bridge Lane Vineyards and picturesque Seabrook Horse Farm, this bucolic home offers the perfect setting for a North Fork getaway.

The Quail’s Nest
A beautifully landscaped tranquil oasis. Newly constructed private two bedroom, one bathroom guest extension to owner occupied house. Guests share large yard and pool with owner, and have private deck and seating area. Private entry and parking. Guest's may enjoy outdoor shower and BBQ. Please note there is no kitchen, however a small fridge, Keurig coffeemaker and microwave, plates/utensils are provided. Conveniently located to beaches, shopping and local restaurants in East Hampton.

Private & Pristine with Pool and Kid’s Playard
INSTANT BOOK/ dates are current. Private and Pristine 3 bed / 2 bath home in the heart of East Hampton set on 1.3 acres. Home features a chef's kitchen, in-ground gated pool, and pure privacy and relaxation. Close proximity to East Hampton Village (5 mins) and East Hampton, Amangansett and Bay Beaches (7mins), Montauk (20 mins), Sag Harbor (15 mins). Kids adore the huge playground! Entire property fenced-in to ensure the safety of kids! Heated Pool open: Memorial Day - Sept 30.

East Hampton Oasis - Pool and Hot Tub
Nestled at the end of a private road in the Springs section of East Hampton, this classic Hamptons home will keep you and your friends/family entertained. Living room with sonos sound system, kitchen, 3 bedrooms, 2 bathrooms, outdoor living area with lounge chairs, a bbq, bar, pool and hot tub. All 3 bedrooms have AC. Towels and linens provided. Washer/dryer available. CLOSE TO BEACH AND EH VILLAGE. The pool is open May 5 through October 5. The hot tub remains open year round.

PRIVATE BASEMENT APARTMENT WITH POOL IN SAG HARBOR
Beautiful basement apartment partially in-ground, with many windows and private entrance is located in Sag Harbor , 3 minutes from village and Heavens Bech by car or 15 minutes walking distance . The apartment has king size bed and comfortable sofa in the living room . In the kitchen you can find coffe maker , toaster , microwave, dishwasher, small fridge , hot plate for light cooking . Tv , WiFi , Airconditoining , access to pool from May till end of the September .

1 prvt pool 2 baths 3 miles to beaches 4 u 2 enjoy
Beautiful, bright, spacious King suite w fireplace, two en-suite bathrooms & private separate poolside entrance. We are just minutes to beaches, boating, golf, hiking, biking, yoga and wineries. Play games, grill or cozy up fireside w a good book or movie. The space is creatively designed with a nod to natural elements and luxe comfort. Sleep your very best on our super deluxe king sized bed w/your choice of pillows. Complimentary coffee/tea/treats

Private Cozy Cottage with Pool / Private Beach
**POOL CLOSES SEPTEMBER 30TH** **POOL opens last week of May** This is a guest house for 1 or 2 adults. Its separate from the main house. Kids are allowed but must bring own sleeping arrangements. You do NOT have to do any chores before checking out. **PETS NOT ALLOWED** I hate to do this but someone ruined it for everyone. Max Occupancy: 4 Guests can only bring 1 vehicle since there is not enough room in the driveway

Exclusive Sag Harbor Compound
A private country compound in heart of Sag Harbor. House just gut renovated with all top of line (all Wolf and Subzero appliances). The main house is 3 bedrooms, 3.5 bath main house PLUS separate large guest cottage (with a King bed, bar fridge, and full bathroom). Gunite pool (i.e., salt chlorinated which makes it feels like clean freshwater). Walk to town, bay beach, public tennis courts, 1000 acre nature preserve.
Popular amenities for Bridgehampton rentals with a pool
House rentals with a pool

Splendid private cottage

Stunning Southampton Star

Perfect Beach Home in Sag Harbor

East Hampton Rental w/ Pool, Moments to Amenities

Brand new house with an all year round hot tub.

The Perfect Summer Beach Home in Sag Harbor

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Secluded Luxury: New Gunite Pool, Walk to Bay
Condo rentals with a pool

Greenport Getaway at Cliffside Condos

1 BR Loft Apt- Montauk Manor- Pools, Tennis & Gym!

Beautiful condo on Long Islands Northfork

Montauk Royal Atlantic Beach Resort North

Montauk Waterfront Condo w/ Sunset Views

Beautiful Waterview Condo on the North Fork of LI

Waterfront Escape | Private Beach, Pool & Views

Beachside Waterview 2Br Condo w/ Pool in Greenport
Home rentals with a private pool
Enchanting Home with Large Decks and Heated Pool
East Hampton Villa | Heated Saltwater Pool & Beach
Perfect Getaway at Sunny Modern Shampton LakeHouse
Saltbox with Separate Poolhouse in Northwest Woods
When is the best time to visit Bridgehampton?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $1,963 CAD | $1,973 CAD | $1,973 CAD | $1,842 CAD | $2,041 CAD | $2,041 CAD | $2,190 CAD | $2,558 CAD | $1,928 CAD | $1,950 CAD | $1,837 CAD | $1,905 CAD |
| Avg. temp | 0 °C | 1 °C | 4 °C | 10 °C | 15 °C | 21 °C | 24 °C | 23 °C | 19 °C | 13 °C | 8 °C | 3 °C |
Quick stats about vacation rentals with a pool in Bridgehampton

Total vacation rentals
Explore 240 vacation rentals in Bridgehampton

Nightly prices starting at
Bridgehampton vacation rentals start at $204 CAD per night before taxes and fees

Verified guest reviews
Over 2,410 verified reviews to help you choose

Family-friendly vacation rentals
220 properties offer extra space and kid-friendly amenities

Pet-friendly vacation rentals
Find 120 rentals that welcome pets

Rentals with dedicated workspaces
140 properties have a dedicated workspace

Wifi availability
230 of Bridgehampton vacation rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Bridgehampton rentals

4.9 Average rating
Bridgehampton stays are highly rated by guests—averaging 4.9 out of 5!
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- Yale University
- Cooper's Beach, Southampton
- Charlestown Beach
- Southampton Beach
- Ocean Beach Park
- Mohegan Sun
- Sunken Meadow State Park
- Hammonasset Beach State Park
- Mystic Seaport Museum
- Foxwoods Resort Casino
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- Long Island Aquarium
- Ocean Beach
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