Vacation rentals with a pool in Woburn

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Top-rated rentals with a pool in Woburn

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Guest favorite

A spacious living room features a large sectional couch and an accent chair, both positioned on a patterned area rug. A wall-mounted TV is visible, with light streaming through the windows, highlighting the natural wood flooring and airy design.

Home in Derry

4.91 out of 5 average rating, 174 reviews

Sanctum by the Lake

Looking for a place to bring the family, or a get-a-away with friends? This is it! From the light and airy design that makes it feel like home to the large pool, hot tub, and lake access, The Sanctum by the Lake has everything you need for a great stay. It is a short 100 yard walk from the lake and a quick drive to Canobie Lake Park and Manchester Airport, 45 minutes to Boston or the NH Seacoast, close to the Lakes Region, White mountains, and great skiing spots as well as the famous NH Outlets.

Guest favorite

A spacious outdoor area features a crystal-clear pool surrounded by a paved deck. Several lounge chairs are positioned nearby for relaxation. The house in the background displays a welcoming design with a cozy porch. Lush greenery provides a serene backdrop to this inviting space.

Apartment in Winthrop

4.96 out of 5 average rating, 302 reviews

Cody's Place Boston Airport Pool/Beaches ParkFree

Retreat, relax, & refresh in your own private entry basement in law apartment of our well bunkered Beach House. BEST LOCATION across from the mighty Atlantic & Iconic Winthrop Arms Hotel/Restaurant. Take in the salty air & breathtaking sunrises. Steps from Ocean Sunrise & Sandy Beach Surf. Walking distance to public transport, restaurants, parks, or Uber/Walk to the center bars & other attractions. Vacation living. Ferry minutes to downtown Boston. 1 of 3 officially licensed AirBnB's in town.

Top guest favorite

The outdoor area features a serene saltwater pool surrounded by lounge chairs, all set against a backdrop of panoramic ocean views. A pergola provides partial shade, and vibrant flowers add a touch of color to the landscaped surroundings.

Apartment in Winthrop

4.96 out of 5 average rating, 236 reviews

Oceanfront Pool. Close to Boston. Free Parking.

Enjoy a relaxing & tranquil beach setting while having quick access to Boston and all it has to offer. Stunning ocean views can be seen from our seasonal saltwater pool and all-season hot tub (exclusive during your stay). We are 4 short miles from Boston & public transportation is easily accessible. Winthrop is a welcome relief from the hustle and bustle of the city, where you can come "home" and wind down to the sound of ocean waves, seaside birds, gorgeous sunrises, and beautiful moon rises.

Guest favorite

An outdoor swimming pool is surrounded by a spacious patio and lush greenery. Sun loungers are arranged around the pool, with a shaded seating area nearby. The house features a multi-level deck overlooking the pool, creating a relaxing outdoor space for guests.

Home in Hopkinton

4.95 out of 5 average rating, 153 reviews

Hopkinton Mass 3+ Bedrooms - Great location!

This my home in which I am now an "empty-nester". I have 3 bedrooms available, each with a Queen bed, plus a room over the garage with 2 futons and a mattress. NOTE: I live here and will be home during your stay. You'll have access to a private bathroom and the rest of the house: kitchen, dining room, living room, etc. NO pets allowed My place is close to Boston, Worcester, Providence, state parks, etc. Good for singles, couples, business travelers and families. Great pool and hot tub!

Top guest favorite

A spacious pool area is highlighted by a clear, inviting blue water surface. Surrounding the pool are comfortable lounge chairs and various patio seating. Lush greenery and colorful flowers enhance the landscape, while the light-colored exterior of the building offers a charming backdrop.

Apartment in Ipswich

5 out of 5 average rating, 31 reviews

Dunover Farm. One bedroom apartment.

Welcome to our fully renovated apartment on our charming farm retreat near breathtaking Cranes Beach! 1-Bedroom, 1-bath private apartment Outside, you'll find a spacious patio and pool area where you can soak up the tranquility of the farm. Sip your morning coffee with the sheep, or savor a glass of wine in the evening as you enjoy the view of the horses. We are close to the quaint town of Ipswich, minutes to Cranes Beach, minutes to MBTA commuter rail train, and only 40 minutes to Boston.

Superhost

A well-maintained outdoor pool area is surrounded by sun loungers, providing ample seating. Bright blue umbrellas offer shade above the loungers. The pool features a shallow entry and is accompanied by a small water slide and safety equipment nearby.

Apartment in East Boston

4.82 out of 5 average rating, 153 reviews

Stylish and Cozy at Revere Beach

Unwind in the stylish Studio apt in the heart of Revere. Enjoy the apartment all to yourself and your family. The city is full of award-winning restaurants, bars, shops, historic landmarks, and attractions. Adventure through Revere and the metro Boston region easily from this prime location with very close walking distance to Blue Line subway station and Revere Beach. ✔ Fully Equipped Kitchen ✔ Comfortable Bedroom w/ Full Bed ✔ Office Desk ✔ High-Speed Wi-Fi ✔ Free Parking ✔ Pool ✔ Gym

Guest favorite

An indoor pool is surrounded by light blue walls and gray tile accents. Natural light filters in through large windows, illuminating the water's surface. Steps lead from the pool to a door that opens to the outside area.

Home in Hampton

5 out of 5 average rating, 37 reviews

Sleeps 10, Indoor Pool, Hot Tub, Pups Ok

⭐⭐⭐⭐⭐ Indulge in luxury in this 4-bedroom beach home in Hampton, NH, just a short walk to North Beach, boasting stunning water views of Mill Pond & Meadow Pond. Relax in the indoor heated pool and unwind in the NEW hot tub on the private deck, all while surrounded by the natural beauty of the marsh. Don't forget to check out previous guest reviews in the additional photos section. “Although we are a pet friendly property we do charge a pet fee of $100 for two pups under 50 pounds.”

Top guest favorite

A serene backyard pool area is highlighted, featuring clear blue water and a smooth surrounding patio. Sunlight casts a warm glow, while a sitting area with lounge chairs and a glass-enclosed indoor space adds comfort. Lush greenery and blooming flowers frame the area.

Cottage in Lakeside Marblehead

4.98 out of 5 average rating, 112 reviews

House with Pool, 4 Houses from Harbor, Fort Sewall

Marblehead Harbor is just 4 houses away from this beautiful antique home with a backyard pool in Old Town Marblehead. This quaint cottage is surrounded by a beautiful garden and is just steps away from The Barnacle Restaurant. Walkable to attractions like Fort Sewall, Fort Beach, Gas House Beach and local shops and restaurants. Car-free convenience in Old Town Marblehead. Perfect for couples or families seeking a charming and convenient getaway that offers off-street parking.

Superhost

A newly renovated home features a heated private pool surrounded by a concrete patio and green lawn. Lounge chairs and a table with umbrellas are positioned conveniently for relaxation. A fence ensures privacy, and neighboring houses are visible in the background under a clear blue sky.

Cottage in Newburyport

4.93 out of 5 average rating, 114 reviews

Sunset Waterfront Privacy Beach

Newly renovated waterfront with private beach and panoramic views. Enjoy the private pool (heated June through September). Unmatched privacy and large outdoor living. Front row wildlife views of marsh. Bikes to venture out and discover the island. Evenings by the firepit watching the tides roll in. Amazing sunsets! Private sleeping loft in bedroom 3 perfect for older kids. Modern kitchen with a washer/dryer combo. Wake up to a fresh Tea or Coffee.

Superhost

A bright pool area is depicted with a crisp blue swimming pool surrounded by a spacious concrete deck. Lounge chairs are arranged near the pool, and a small building stands nearby, accompanied by trees and a well-maintained lawn, suggesting a serene outdoor environment.

Home in Bedford

4.67 out of 5 average rating, 33 reviews

Bedford Retreat: pool, fenced yard.

Peaceful 1 bedroom retreat. Enjoy the privacy of your own home. Sit poolside, enjoy the luxurious king size bed, fire pit, sit on the porch and watch the wildlife. Enjoy the well equipped kitchen, large screen TV and proximity to local restaurants. A second sleeping room with a queen bed is available on the lower level for a small additional guest charge Check-in is after 4:00 PM EST. Pool will be open early June and close in Oct.

Guest favorite

A tranquil outdoor pool area is surrounded by lush greenery, featuring a swimming pool with a waterfall. Colorful chairs in pink and turquoise are positioned nearby, inviting relaxation. A hot tub is situated adjacent to the pool, contributing to the serene atmosphere.

Apartment in Holliston

4.96 out of 5 average rating, 120 reviews

Lake Link

Beautiful fully stocked 2 BR apartment located in Holliston Historic District. Top of the line swimming pool with waterfall and hottub (May 31-Sep 30). Full kitchen, full bath, washer/dryer, central heat and AC, fireplace, wireless internet, Cable TV with almost all premium channels available, private driveway and entrance. Sorry, but no pets allowed. Note: COVID19- We require all eligible guests to be vaccinated or have 72 hr negative test.

Guest favorite

The backyard features a tranquil swimming pool with sunlit reflections, surrounded by elegant outdoor seating arranged on a stone patio. Large windows in the main house offer views of the inviting outdoor space, enhancing the serene atmosphere.

Home in North Andover

4.94 out of 5 average rating, 152 reviews

Nana-tucket Inn

Charming historic town, home of Brooks School and Phillips Academy, 30 minutes to Boston and Seacoast. Families will enjoy our children’s park and town park, just a short walk from property. Enjoy pastural views while relaxing poolside (availability May 1 - Oct 1)in a quiet & private backyard setting. Hot tub is also open May 1 til Nov 1. Seven minutes to commuter rail for those who desire traveling into Boston, no hassle!