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

Ocean Edge 2 Bed 2 Bath, Golf & Free Resort Access
Enjoy this 1,000 SF, 2 bed, 2 full new marle tile bathrooms, 2 showers, at Ocean Edge, right in the middle of the golf course. This Airbnb is a full member of the Ocean Edge Resort and allows you access to Ocean Edge golf, and free resort access included up to 6 guests to swimming pools, tennis, gym & pickleball. No one lives here, it is absent of personal items. From the moment you enter, you will know that you have made a great choice and that your time here will be above your expectations.

Ocean Edge Resort/Pool access/2bedroom-2bath Condo
Recently renovated end unit townhouse located in the heart of The OE Villages. Beautiful views towards the golf course, and southern exposure with lots of natural light, A/C, W/D and private patio with Weber grill and outdoor furniture. Sports Membership so Guest passes are available for purchase at Linx for use of pools, hot tubs and gyms. Additional costs for use of courts may apply. Bike rail trail, Ice cream store, great restaurants, coffee, beaches and Kayak/Bike rentals are all close by.

Private Pool, near beaches, 3 BR/3 BA, Central Air
Enjoy the Barnstable historic seaside village of Cotuit in this sprawling house with central air, nestled in the pines on a quiet street with private gated (unheated) pool, lg. backyard, firepit, ample parking, just blocks from Main St, Ropes Beach, scenic ocean views, fort playground, and Kettleer baseball. Each bedroom has a TV and ensuite bathroom! Relax in the seasonal sunroom overlooking the pool; grill burgers on the patio. Max. 9 (6 adults). Pool open 6/20-9/15/26. The reviews tell all!

Family Friendly Hideaway
Prepare to be wowed by this amazing two-story home built for indoor and outdoor entertaining. Prepare a meal at the outdoor kitchen while the kids play in the heated plunge pool. Top off a great day sitting by the fire and watching a family movie under the outdoor pavilion. Step inside to the gourmet kitchen and large great room with plenty of room to spread out. Head up to the game room for some ping pong, air hockey and video games. Linens, towels, beach towels, 4 beach chairs included.

Ocean Edge Resort-Pool Access-End Unit-2 bdr/2 bth
2nd floor Ocean Edge end unit condo located in the heart of Brewster with access to OE resort amenities: pools, gyms, tennis courts, as well as access to resort activities (fees apply). Easy access to Cape Cod Rail Trail for bicycles. Scenic route 6A offers arts & crafts galleries and local shops. A 10 minute car ride to a 36 hole Captains Golf course. Short ride to 10 Brewster bay beaches famous for tidal flats. A 30 minute ride to Cape Cod National Sea Shore. Welcome to your Happy Place!

Modern Cape, Private Heated Pool, Beach, Golf
Welcome to your perfect vacation/reunion in the center of the Cape. Min. to 3 golf courses, 5 ocean beaches, lakes, park, trails. Bright modern quality home available year-round. Vast serene private 1.5 acres adjacent to conservation land. Lighted Private heated saltwater pool Mid May to End Sept. Bocce Court, Putting green, Corn hole, Hammock, Outdoor shower, AC. Expansive double deck with awning. Beautiful indoor/outdoor dining/entertaining. All essentials provided. 7+ free parking.

Rock on Wellfleet!
A wonderful Wellfleet location! This second floor rental has a spacious bedroom with a queen bed, bathroom with a tub and living area with a well stocked kitchen. You would have the whole upstairs to yourself with a private door to come and go. You are also invited to use our pool at anytime! We're located very close to the Cape Cod Rail Trail for miles of bike riding, PB Boulangerie Bistro, Marconi Beach, the iconic Wellfleet drive-in and so much more. Bedding, towels and essentials provided.

Sea Salt Studio - Steps to Glendon Rd Beach
Funky studio (Unit #1) only 175 yards from a white sand beach on Nantucket Sound. Soak up the sun at the beach, relax by the pool or enjoy a relaxing cocktail on your own private patio. This studio is equipped with a fridge, microwave and gas stove as well as a fully stocked kitchenette and cable/Roku TV. A futon couch offers extra sleeping space, if needed. Outside, enjoy a natural gas grill. Walk or bike to multiple restaurants, ice cream shops and all the amenities Dennis Port has to offer.

Townhouse at Ocean Edge 2B/2B + Loft
Experience resort-style living at its finest! Tucked away just a 10-minute drive to the beach, this delightful townhouse offers the perfect blend of comfort and convenience. With two bedrooms, two baths, and an additional cozy loft space, there's ample room for relaxation. Enjoy lounging on the patio, take a refreshing dip in one of the resort pools (for an additional fee paid directly to Ocean Edge) or head to the beach for some sun and surf. Your ultimate getaway awaits!

The Holly Cottage
Welcome to Centerville, enjoy this fully equipped 1 bedroom 1 bath home with an easy walk or ride to just about everything. Enjoy the nearby ocean and beaches, or take a ride downtown to Main Street for dining and entertainment. Only a short distance to the ferries for a day trip to the islands and you can be back in time to catch a concert at the Melody Tent. Enjoy your days by the pool and your evenings grilling out on the large deck or chatting with the koi fish.

Great Location. Near Beach & Main Street. Unit M1
Our home-away-from-home accommodations include this charming studio with lawn space, a private deck with outdoor furniture and a gas grill. The cottage is comfortably furnished and features a small kitchen. This cottage has a queen bed and a table with sitting area. The kitchen is nicely updated with updated with beautiful granite countertops and stainless steel appliances including an stove/oven, microwave, mini-fridge, toaster, coffee maker. Keurig, and kettle.

Wellfleet~Beautiful One Day Perfect The Next
Are you looking for the perfect getaway in charming Wellfleet? This two-bedroom cottage is located in a private, detached cottage village. Enjoy the beautiful SEASONAL in-ground pool (OPENS July 4th & CLOSES LABOR DAY) and a welcoming family-friendly atmosphere. The cottage is centrally located with a five-minute drive to both bay and ocean side beaches, freshwater kettle ponds, Wellfleet center, and the rail trail!
Popular amenities for Brewster rentals with a pool
House rentals with a pool

Walk 2Beach, Pool, Hot Tub, GameRoom, PetsOK

Harwich Haven: Pool & Fire Pit

Family Fun- Games, Pool & HotTub, Dogs ok! Slps 10

Exclusive New Seabury Home w/ Heated Pool ⛳️🏖🦞☀️🐠

Mansion with Heated Pool Near Ocean

Centerville Oasis, Heated Saltwater Pool!

4 BD slice of Harwich Heaven

Game Room- Movie Projector Room- Fire Pit
Apartment rentals with a pool

Cozy Studio Just Steps Away From the Beach!

1BR 2nd Floor Condo with pool

Comfy Cape Escape! Spacious, Cozy, Close to Beach!

Ocean Edge: 2 bed/2 bath - Pools & Resort Access

Stylish & Modern Studio Condo - Steps to the Beach

Hidden Hideaway

Mary's Cape Escape

Mid Cape Cod, 3 Season Haven by Bass River
Other holiday rentals with a pool

Beachside Condo with Balcony - Oceanside Condos

Our families slice of heaven

18 Menemsha Rd., Popponesset, Pool, 3-Beds, 4 bath

1 bedroom apartment located 5 minute walk to beach

Coastal Retreat in Sandwich -Pool Access, Dogs OK!

Hyannis Port Coastal Escape – Pool & Walk to Beach

Home w/ golf view, salted heat pool, mins to beach

Renovated ranch with pool access
When is the best time to visit Brewster?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $377 SGD | $254 SGD | $376 SGD | $383 SGD | $515 SGD | $639 SGD | $713 SGD | $833 SGD | $544 SGD | $508 SGD | $377 SGD | $637 SGD |
| Avg. temp | 0°C | 0°C | 3°C | 7°C | 12°C | 17°C | 21°C | 21°C | 18°C | 13°C | 8°C | 3°C |
Quick stats about holiday rentals with a pool in Brewster

Total holiday rentals
Explore 60 holiday rentals in Brewster

Nightly prices starting at
Brewster holiday rentals start at $217 SGD per night before taxes and fees

Verified guest reviews
Over 1,760 verified reviews to help you choose

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

Pet-friendly holiday rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
30 properties have a dedicated workspace

Wifi availability
60 of Brewster holiday rentals include wifi access

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

4.8 Average rating
Brewster stays are highly rated by guests – averaging 4.8 out of 5!
Destinations to explore
- Plainview Holiday rentals
- New York City Holiday rentals
- Tuckahoe Holiday rentals
- Long Island Holiday rentals
- Boston Holiday rentals
- East River Holiday rentals
- Hudson Valley Holiday rentals
- Jersey Shore Holiday rentals
- Philadelphia Holiday rentals
- South Jersey Holiday rentals
- Pocono Mountains Holiday rentals
- The Hamptons Holiday rentals
- Rentals with a kayak Brewster
- Pet-friendly rentals Brewster
- Rentals with a fireplace Brewster
- Rentals with lake access Brewster
- Apartment rentals Brewster
- Cottage rentals Brewster
- Flat rentals Brewster
- Rentals with beach access Brewster
- Rentals with a firepit Brewster
- Waterfront rentals Brewster
- Villa rentals Brewster
- Rentals with a washing machine and dryer Brewster
- Rentals with a hot tub Brewster
- Rentals with a patio Brewster
- Beachfront rentals Brewster
- House rentals Brewster
- Family-friendly rentals Brewster
- Rentals with outdoor seating Brewster
- Rentals with pools Barnstable County
- Rentals with pools Massachusetts
- Rentals with pools United States
- Cape Cod
- Mayflower Beach
- West Dennis Beach
- Craigville Beach
- East Sandwich Beach
- Duxbury Beach
- Onset Beach
- Coast Guard Beach
- New Silver Beach
- Pinehills Golf Club
- Sandy Neck Beach
- Cahoon Hollow Beach
- Nickerson State Park
- Lighthouse Beach
- Popponesset Peninsula
- Cape Cod Inflatable Park
- Saquish Beach
- Nauset Beach
- Race Point Beach
- Skaket Beach
- Sea Gull Beach
- Marconi Beach
- Sandwich Glass Museum
- New Bedford Whaling Museum




