
Holiday rentals with a pool in York
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in York
Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

Attitash Retreat
Cozy spot for 4, plus your furry friend! (Must be 21 to check-in, no cats) Less than a mile from Attitash Mountain Resort, this spot is home base for your next adventure. IF YOUR DOG IS JOINING YOU, please provide advanced notice, a $25/night pet fee for the first 4 nights (max$100), that rabies vaccination records be provided at check in, and that your dog have access to a crate for times that you must leave him/her behind! One dog is permitted per room, no cats. Thank you for understanding.

Centrally located Ocean Towers condo in Ogunquit
This charming and comfortable 1 bedroom 1 bath condo includes a generous living area complemented by an updated kitchen. Located on Rt 1 at the Ocean Towers condo complex. Trolley stop in front of condo. Walking distance to restaurants, shops, beach, the Marginal Way, Perkins Cove & more! Swimming pool, on site coin-operated laundry, free parking, cable, 2 ACs, & Wi-Fi. The bedroom includes a Queen bed, TV has a HDMI cable for streaming. Linens provided. *Renters need to bring their bath towels.

Portland & Beach & Lighthouses! Romantic! Lovely
Location! You get the BEACH + Portland in minutes! HUGE BEDRM Romantic canopy bed w/ lux linens Chaise lounge couch turns into twin bed TV Giant mirror for weddings etc 35’ Great Rm w/ TV Kitchen *quality pots etc New Q Sofa Bed Priv entrance Beachy Light filled tall ceilings Spacious for 2-can fit 5 pond/bridge firepit 2 decks+patio Teak Furniture Open views New bthrm A/C Parking No stairs/Garden Level All in Cape: Crescent Beach 2 Lights State Pk Portland Headlight Prtlnd 8 min! 210780

Designers Dream Home with Pool!
Discover this brand-new, beautifully appointed 2-bedroom home nestled within a secure, private community surrounded by 200 acres of preserved natural beauty. Enjoy full access to outdoor heated pools, a clubhouse featuring a game room (with ping pong, foosball, shuffleboard, and a poker room), and a fully equipped fitness center to keep you on routine. Mingle with fellow guests at the clubhouse or relax in your peaceful, private backyard, and enjoy the perfect balance of activity and serenity.

Everything's "Well Ashore"- 1 mile to Wells Beach!
Welcome to 'Well Ashore', a charming 1-bedroom, 1-bath efficiency condo just 1 mile from the breathtaking Wells Beach- One of Maine's 7 mile pristine sandy beaches. Ideal for couples or small families, this cozy retreat features a serene, nautical-inspired ambiance perfect for relaxation. Our condo is 4 miles from The Marginal Way, one of New England's most cherished coastal walks. This 1.25 mile scenic path offers stunning ocean views with benches, and an easy access to downtown Ogunquit.

Romantic New England Historic Schoolhouse c1866
Winner of Maine Homes Small Space Design Award 2023 We are located on the private 80-acre Shapleigh Pond in the Southern Maine, an hour from Portland and two hours from Boston. Experience a bygone era in this restored Schoolhouse circa 1866 with many original details such as oversized glass-paned windows, wood plank floors, chalkboards, tin ceiling and more. Modern amenities such as fireplace, private hot tub, fire pit, gas BBQ and access to our pool (June-Sept), pond and tennis court.

Cozy Cottage with Ocean Views, Wells Maine
Ocean breezes, panoramic views of the Atlantic, comfortable cottage to relax & enjoy your time in Maine, what more could you ask for on a getaway?! This cozy cottage for 6 boasts near panoramic views of the Rachel Carlson preserve and the Atlantic Ocean. Tastefully decorated and newly updated, our cottage offers AC/heat, ceiling fans, fully equipped kitchen with dishwasher, outdoor gas grill, cable TV in all rooms, WiFi, cabled phone, skylights, in unit W/D & a large screened in porch.

OOB Oasis - Spacious 5BR private Retreat w/ Pool
Welcome to our stunning home and your private oasis in Old Orchard Beach! Just 5 minutes from the ocean, this expansive custom-built retreat offers 3 suites (each with its own private bath), a gourmet kitchen with high-end appliances, a sprawling open floor plan, and ample parking for large groups. Step outside to enjoy a large fenced backyard, spacious deck with BBQ grill, and sparkling in-ground pool—perfect for summer fun, fall gatherings, or simply relaxing after a day at the beach.

Tower Suite w/ Hot Tub, W/D, & Parking
This newly renovated, gorgeous, spacious suite, located on the 3rd floor of our 1865 mansion, is just 10 mins to downtown and the airport. Relax by the firepit or soak in our hot tub and enjoy our gardens. We are owner-operated. The suite includes a newly renovated bath with rain shower and radiant floor heating; W/D; lounge and kitchenette w/ work table; and a large bedroom. Our half-acre yard provides ample space for privacy. Level 2 EV station is available #allarewelcome

Maine Coastal Village Getaway
Experience tranquility at this beautiful condo in Cape Porpoise, Kennebunkport. It offers a modern kitchen, cozy living space, and a stunning deck overlooking Cape Porpoise Harbor. Enjoy the serene landscaping and shared pool. Close to a grocery store, top-notch restaurants, shops, and a scenic walk to Cape Porpoise pier. Just a short drive to Kennebunkport town center, beaches, and Goose Rocks Beach. Book your stay at 15 Langsford Road today for an unforgettable getaway!

Steep Falls Escape, river & falls just steps away
Bright and pleasant 1 bedroom apt with separate entrance, gas fireplace, enclosed porch and large kitchen. Spacious yard to enjoy with pool, fire pit, grill and outdoor seating. Steep Falls is a rural village. Our home is a 5 min walk to the Saco River a favorite destination for canoeing, kayaking or tube floating (after the spring run off!) It is just a 10 min drive to the boat launch for Sebago Lake, one of Maine's largest and most beautiful bodies of water.

The Haven at Doherty Homestead
Our pricing is transparent; there are no cleaning fees or surprise costs. Looking for a cozy place to crash after adventuring about? One hour from Boston, the ocean or the mountains, we are 10 minutes from city life as well as local hiking spots. Prefer a restful respite? Our backyard is your oasis; firepit, meditation treehouse, hammocks and patio area complete with a dining table, outdoor TV and lounge furniture.
Popular amenities for York rentals with a pool
House rentals with a pool

Nana-tucket Inn

Faith Lane with community pool

Locke Lake Ski & Swim

Sanctum by the Lake

Cozy Beach Cottage - Wells, ME

"Good Vibes" 4 Wonderful Seasons @ Portland Home!

Maritime Meadows - Charming Resort-Style Home!

Fireplaced Mountain King Suite w/Hot Tubs & Pools
Apartment rentals with a pool

Attitash Studio | 5min to Storyland| Pools

Cranmore Condo | Pool, Hot Tub & Minutes to Town

Steps from Beach | Pool | Parking | Sleeps 6

AttitashResort! 1-flr, studio, secure check-in

Slope-side White Mountain Oasis

KimBills’ on the Saco

Spectacular Mountain View’s

Relaxing Beachside Condo with Pool at Wells Beach
Other holiday rentals with a pool

Ogunquit Modern Poolside - 1BR

Four Story Townhouse With Ocean View 55

1 bedroom with pool, walk to the beach.

Studio condo, 2 queen beds, Laundry, restaurants

Condo in Old Orchard Beach

Cottage 2 @ Coast Village Inn

Beach Bliss, Amazing location!

Lux home near Rt 3/MHT/mountain/lake/ocean/Boston
When is the best time to visit York?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $327 SGD | $425 SGD | $290 SGD | $261 SGD | $256 SGD | $352 SGD | $452 SGD | $452 SGD | $337 SGD | $258 SGD | $314 SGD | $311 SGD |
| Avg. temp | -5°C | -3°C | 1°C | 7°C | 13°C | 18°C | 21°C | 20°C | 16°C | 10°C | 4°C | -1°C |
Quick stats about holiday rentals with a pool in York

Total holiday rentals
Explore 140 holiday rentals in York

Nightly prices starting at
York holiday rentals start at $131 SGD per night before taxes and fees

Verified guest reviews
Over 3,170 verified reviews to help you choose

Family-friendly holiday rentals
40 properties offer extra space & child-friendly amenities

Rentals with dedicated workspaces
30 properties have a dedicated workspace

Wifi availability
140 of York holiday rentals include wifi access

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

4.8 Average rating
York stays are highly rated by guests – averaging 4.8 out of 5!

Nearby attractions
York’s top spots include Ogunquit Playhouse, Strawbery Banke Museum and Mount Agamenticus
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- Hampton Beach
- Ogunquit Beach
- Sebago Lake
- Wells Beach
- Scarborough Beach
- York Harbor Beach
- Long Sands Beach
- Good Harbor Beach
- Canobie Lake Park
- Crane Beach
- Jenness State Beach
- Rye North Beach
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- Salem Willows Park
- East End Beach
- Dunegrass Golf Club
- Funtown Splashtown USA
- Salisbury Beach State Reservation
- Willard Beach
- Cliff House Beach
- Wentworth by the Sea Country Club
- Short Sands Beach
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- Bear Brook State Park




