
Holiday rentals with a pool in Middlesex County
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Top-rated rentals with a pool in Middlesex County
Guests agree: These homes with a pool are highly rated for location, cleanliness and more.

Courtyard Garden | Pool | BBQ+Fire Tbl | 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.

Cozy Private Studio Unit w/ Laundry and Parking!
Almost every guest describes my place as cozy, which was the feeling I was going for when I designed the space! You'll love this good sized 300 sq. ft PRIVATE 1 bedroom studio. This unit has its own entrance w/ punch code door, full bathroom, large walk-in closet, mini fridge, freezer and microwave. It has one parking spot in the driveway and a washer /dryer. The backyard is shared but the unit has a private patio. Rental is attached to a single family home. (Please note: No full kitchen)

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!

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.

Pool•1000mbpsWiFi•DeepTub•Fireplace•Full Kitchen
Welcome to Echo Point™️ Luxury Home 15min drive to Wachusett Mountain [The Space] Amenities and services → large 40x20 Pool (memorial day-9/1)SemiPrivate → Well-equipped kitchen → King Bed | Queen Bed | 2 Full beds → AC in all main rooms (memorial day-9/1) → Netflix/Roku → 6 seat Dining → On-Site Parking → Garden patio → Prep Vanity Add my listing to your Wishlist by clicking the ❤️ in the upper-right corner. Entire space is included in this rental. Please, make yourself at home.

Country Cottage in the City
This poolside cottage is a country retreat in the city. We are nestled into a small bit of woods on top of the "hill" as it is called locally. The cottage is a studio apartment that has a microwave and mini-fridge as well as sitting area and table. It has a lovely view of the pool and gardens. Besides the pool, there are two garden ponds where we keep ornamental fish. Outside the garden fence there is often a parade of various types of birds, bunnies and even wild turkeys and deer.

the house of id; vintage shop, accessible space
🏡🚨‼️ Now Featured in The Boston Globe ‼️🚨🏡 Stay. Id's design is informed by our firsthand experience of living with a chronic/invisible illness. To us, accessibility means joy at your fingertips; and participation without overexertion. Unmask. Shop. We did the legwork, filling the house with buyable treasures. Live with the pieces you love. Then take them home. Take Part. Some of the house is experiential. Change hardware. Move art. Bake for the community. Get involved.

Farmhouse Guest Apartment
Welcome to our quiet private guest apartment! Our property, is surrounded by fields, woods, gardens, and a pond. You will enter through a shared entrance & stairway to the second floor in our home, but have an entire 725 sq. ft. guest apartment all to yourself that includes a living room, full kitchen, bathroom, and large bedroom with a desk. It has ample light with views of fields, stone walls, Christmas trees and our barn. Out back we have a pool, table & chairs you may use.

Spacious vacation unit in premium suburban town
Weston is one of Boston area's most desirable towns. <30 min to downtown Boston with a lot of open space. Centrally located with easy access to highways, train stations, etc. Next to a park with hiking trails, this is a secondary unit (Duplex units) with its own separate entry/exit. 3 bedrooms (one on lower level, two on 2nd level), kitchen, 2 baths (both on lower level). ~2000 square feet of space. Some seasons (including some winters) we have hens in the backyard...

Exquisite 1 Bedroom Suite-Charming,W/Private Entry
An exquisite and convenient I BR Modern suite nestled between Boston and Worcester is available for you. Bright and charm w/ a . Beautiful kitchen, remodeled bathroom and a bedroom. Private entrance w/ it’s lovely courtyard to sit outdoor, a free parking spot/ WiFi. The apartment is conveniently located to Babson and Wellesley College, both within 7 miles , FSU is 1 mile train station 2 miles , easy drive to Cape Cod. For all travelers & enjoy your stay her !

The Drew : Vibrant • Comfortable • W/D • City View
Experience Boston in a beautiful luxe jr. 1 bedroom unit! Just a 5 min walk from the T and close to Boston College/Harvard. Unit Features -> Blazing Fast WiFi -> 65” SmartTV with Streaming -> Fully Stocked Kitchen -> Washer & Dryer -> Comfortable Queen Bed -> Game rooms across the property Air bed and single rolling cot available on request. Ideal for business travelers, couples, nurses, and anyone seeking comfort and peace in Boston.

Private Luxury Retreat | Pool · Gym · Parking
Discover your exclusive retreat in Everett. Immerse yourself in sleek, curated living with designer finishes and resort‑style amenities for an unforgettable stay. Highlights: • Steps from downtown Boston via easy Silver Line & Route 1 access • Sparkling pool with cabana seating and courtyard fire pits • 24/7 state‑of‑the‑art fitness center & dedicated yoga studio • Private music room, co‑working pods & on‑site community pet spa
Popular amenities for Middlesex County rentals with a pool
House rentals with a pool

Spacious quiet Newton Villa *Easy Boston Access!

Beautiful Spacious 4BRM House!

Theatre | Arcade | Pool w. Free 3 Car Parking

Shared Hot Tub: Historic Cottage, Walk to Elm Park

Explore Boston in style! Dream home (STR-26-3)

Hidden Gem near Boston w/ Private lake access

Private/Quiet Single Family Home

Billerica Colonial - 5 Bedroom Home
Other holiday rentals with a pool

Cozy, with Lots of Space

Brand New Luxury Retreat w/ Pool & Fitness Center

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Cozy 1BR Near Boston w/ Pool & Gym

Serenity - 36’ Aft Cabin Carver

“Luxury 2BR Cambridge | Pool + Parking”
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- Fenway Park
- Harvard University
- Hampton Beach
- TD Garden
- Gillette Stadium
- Boston Common
- Boston Seaport
- Revere Beach
- Boston University
- Boston Convention and Exhibition Center
- Freedom Trail
- New England Aquarium
- Canobie Lake Park
- MIT Museum
- Duxbury Beach
- Northeastern University
- North Hampton Beach
- Monadnock State Park
- Crane Beach
- Quincy Market
- Tufts University
- Harvard Square
- Roger Williams Park Zoo
- Prudential Center
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