Holiday rentals with a pool in Massachusetts

Gather, Cook & Unwind, 3BR, Fireplace

A private resort — without leaving Worcester. Heated pool, fire table, garden courtyard … your own enclosed escape. ★ "Tania’s place was much more than a place….it was a full on fabulous experience." 🏊Heated Pool (to 81F) 🌿 Courtyard w. lounge + garden 🔥Patio w/ Zen fire table* 🍽️ Natural gas + charcoal grills 💧 Reverse osmosis water filter 66” smart TV projector ❄️ Central air conditioning 🔥Indoor gas fireplace 📶300+ Mbps WiFi For non-smokers. No smoking/vaping inside or outside.

Farm Living

We offer a quiet country setting on a small working farm, with cows, horses, pigs, goats, donkeys, peacocks, emu, rabbits, dogs, chickens, ducks and wildlife strolling now and then. There’s opportunity to interact with the animals. Pack n play available for little ones upon request and another twin fold up bed. We truly want all of our guest to enjoy all the farm has to offer and enjoy the peacefulness. Please inquire about kayak rentals. We also have a game room available to rent. See photos

"Cape Escape" luxury home w/pool & beach access.

Welcome to the Cape Escape! Enjoy views of Spectacle Pond from the 70 ft. deck of this recently renovated 5 bed/3 bath spacious home meeting all your needs! Relax by the in-ground pool in the private enclosed yard. Enjoy nights around the fire-pit. Directly across the driveway you can enjoy kayaking, sunbathing & swimming at the neighborhood beach. Within 6 miles of the home you will find the historic Sandwich boardwalk, Ocean beaches, Cape Cod Canal and more! Perfect for family gatherings!

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 4 futons/mattresses. 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!

The Murthy : Bright • Spotless • W/D

Enjoy Boston in this elegant suite for long and short stays. Just a 5 min walk from the T and close to Boston College/Harvard, you can tastefully engage with all of Boston. Unit Features -> Blazing Fast WiFi -> 65” Roku TV Living Room -> 50” (x2) Roku TV Bedroom -> Fully Stocked Kitchen -> 2 Queen Bed -> 1 Twin Bed -> 1 Sleeper Sofa Rolling cot and air mattress available on request! Ideal for business travelers, couples, nurses, and everyone looking to experience Boston in style!

1790 Stone Manor Farm

This historic New England farm and home is on almost 7 acres of land with mature gardens and places to hike, it is a warm and inviting place to spend lovely summer days by the pool and enjoy warm nights by the fire in the fall and winter. Kitchen and bathrooms all renovated. Located centrally in Ma- 90/495 interchange. Located 45 minutes from Boston, beach, history, mountains, lakes, & NE sports. This home is in historic Hopkinton, where the Boston Marathon starts, center of MA.

The Secret Garden 4 Bedroom, 7 Bed 3 Baths

This beautiful 2.5 acre fully fenced in private property has gardens, an in-ground pool & pool house with an outdoor heated shower. Our home offers 2 kitchens, dining room seating 12, a great room, 3 bedrooms with private sitting areas & lower level with 2 bunk beds (bottoms are full beds) & exercise area. Outside are 2 grills & a fire pit. We are 3 miles from the beach, shopping/cafes, 45 minutes from Boston (on a train route) and 20 minutes to Cape Cod.

NE Historical Mansion-pets and pet lovers welcome

Enjoy seamless check-in and a private 1,000 sq ft space on the third floor of our historic Victorian home. Includes 2 bedrooms, bathroom, open hallway, and a combined living/dining/kitchenette area (no sink). Pet-friendly, updated, and comfortable year-round. Accessed via the back staircase; only the entry/hallway is shared. 3rd and Top floor is strictly for guests only. Just 5 min to I-91 and Pike, 15 min to Northampton 15 min to Big E.

Historic 1 Bed/In Town/Best Location/Hot tub/deck

Please do not book weekends, holidays, or summer dates in advance. This 1-bedroom is only offered to fill midweek gaps when the full home isn’t booked. Beautifully restored historic home in the heart of town—steps from the Pilgrims' first settlement, ocean, restaurants, shops, and more. Located on Town Brook near the Gristmill, with a deck, firepit, hot tub, grill, cozy bed, and working wood stove. Clean, comfortable, and full of charm.

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!

Seaview Summit | Ocean Views, Indoor Pool, Beach

Perched above the coastline with panoramic Atlantic views, Seaview Summit House is Plymouth's premier oceanfront retreat. Designed for discerning travelers seeking serenity, space, and sophistication. With a heated indoor pool, expansive outdoor living areas, and direct beach access just moments away, this stunning property delivers a five-star experience in every season. Book your stay today. You'll be glad you did.

Quiet Oasis In The City

Forget your worries in this spacious and serene space. We are right in the city but you'll feel miles away. This two level guest home is surrounded by nature and very relaxing. Two bedrooms and two baths. Two king sized beds. One full bath with oversized tub downstairs. Upstairs bath with standing shower. Full kitchen and coffee and tea. Hot tub is included with BNB. Pool is a separate rental. Message for details.