
Vacation 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.

Cape Cod Condo,Walk to Beach, near Nantucket Ferry
Enjoy your next beach vacation at this charming cottagecore-style condo located in the quintessential seaside town of Harwich Port, just a short walk to nearby Wyndemere Bluffs beach.This delightful beach cottage includes 1 bedroom, 1 bathroom, with an additional queen pull out to accommodate 2-4 guests. Grill out on the porch, take a stroll down Main St for ice cream or lobster rolls, or take a dip in the private community pool (steps from your front door)!Nantucket ferry 1 mile down the road!

Heated Pool. Hot Tub. Game Room. Beach Nearby!
Welcome to The Tide Watch - our luxurious retreat, perfect for families or a group of friends! This stunning home features high-end furniture, a pool, hot tub & games including ping pong & air hockey. With kid-friendly amenities, everyone will feel at home. Relax, play & create unforgettable memories in this upscale oasis designed for fun & relaxation! Walk to small neighborhood beach 3 min drive to Jacknife Beach 6 min drive to downtown Chatham Experience Chatham with us & Learn More Below!

Ocean Edge: 2 bed/2 bath - Pools & Resort Access
Welcome to our spacious and well-appointed 2-bed, 2-bath condo with a private patio overlooking the golf course at Ocean Edge Resort. Access to resort amenities (additional fees apply) and restaurants. We acquired this condo in 2023 and are excited to host you! Perfect for families with kids or a group of friends! You will be a short walk from Ellis Landing Beach and CC Rail Trail and a short car ride away from 10 Brewster bay beaches. Route 6A offers shops, restaurants, art galleries 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 6/20-9/15/24. The reviews tell all!

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!

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.

The Sea Salt Studio - Steps to the Beach!
Gorgeous studio (Unit #1) only 175 yards from white sand Glendon Road beach. 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.

Luxury Home w/ Salt Water Pool Overlooking Ocean
Welcome to your dream Cape Cod getaway! Our brand-new, fully renovated 4-bedroom, 5-bath luxury home offers breathtaking views of Buck’s Creek and Nantucket Sound, creating the perfect backdrop for your vacation. Inside, you'll find a stunning cathedral-ceiling living room designed for relaxation and gathering. The chef’s kitchen features a massive 15-foot eat-in island, perfect for family breakfasts or evening cocktails. Each of the spacious bedrooms offers comfort and privacy.

Cape Cod Oasis: pool, hot tub, firepit & grill!
Over 4500 sqft of living space in the heart of Cape Cod, with an inviting pool, a hot tub, magnificent garden and expansive outdoor living space big enough to fit your entire party. Welcome to your own private resort! This beautiful custom-built center entrance colonial has room to roam, both inside and out. 5 beds, 5 baths, eco pool, The building is surrounded by lush landscape and tastefully decorated. Fully equipped chef's kitchen. Short drive to the beach!

Hidden Hideaway
Welcome to Mid Cape Cod. Location, Location, Location. Wake up in the morning and have coffee on your private patio. The view overlooks the well manicured back yard bordered by tress and bunnies running around. After coffee, walk down main street for breakfast and more coffee at 3 Fins. Now that you are hyped, walk across the street and rent a Kayak or SUP for the day. Paddle out the Bass river down to the Nantucket sound. Have lunch next door at Sundancers.
Popular amenities for Brewster rentals with a pool
House rentals with a pool

Sleeps 12 near beach. Hot tub game room

Stunning Cape Home - Inground Pool, 5 Min To Beach

5-bedroom Cape with a pool and yard games.

Beachside Retreat pool&spa bball court

49 Clover Lane, 3 beds, 3.5 baths, pool & firepit

Modern Cape, Private Salt Water Pool, Beaches-Golf

Cape Cod Lakefront Home

Home w/ golf view, salted heat pool, mins to beach
Condo rentals with a pool

Cozy Studio Just Steps Away From the Beach!

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

Ocean Breeze

1BR Condo w/ Balcony in Mashpee, MA

Great Townhouse - Ocean Edge Resort

Beachfront Complex in Hyannis

Oceanfront beach house - Entire 1st floor

Oct + Nov Discount | Central | Private Balcony
Other vacation rentals with a pool

Renovated Cape Oasis W/ New Pool and Game Room!

Waterfront Home w/ Dock, Heated Pool, Kayaks & A/C

Fenced Pool, Fire pit, Outside dining, Coffee bar

Seasonal 27’ Retro Glamping Steps From Bike Trail

4 BD slice of Harwich Heaven

Hyannis Port Coastal Escape – Pool & Walk to Beach

Cozy cottage steps to the beach!

Skip to Beach, Cape Cod Condo!
When is the best time to visit Brewster?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $411 CAD | $277 CAD | $410 CAD | $418 CAD | $562 CAD | $697 CAD | $715 CAD | $728 CAD | $463 CAD | $417 CAD | $351 CAD | $411 CAD |
| 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 vacation rentals with a pool in Brewster

Total vacation rentals
Explore 60 vacation rentals in Brewster

Nightly prices starting at
Brewster vacation rentals start at $223 CAD per night before taxes and fees

Verified guest reviews
Over 1,690 verified reviews to help you choose

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

Pet-friendly vacation rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
30 properties have a dedicated workspace

Wifi availability
60 of Brewster vacation 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!
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