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

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)

Luxury suite with room divider near downtown
Experience Boston in this incredible eye-catching studio. Comes with a room divider for 1 bedroom like feel! Just a 5 min walk from the T and close to Boston College/Harvard, you can engage with all of Boston tastefully. Unit Features -> Blazing Fast WiFi -> 65â SmartTV with Streaming -> Fully Stocked Kitchen -> Washer & Dryer -> Comfortable Queen Bed Ideal for business travelers, couples, nurses, those in hospital treatment and everyone looking to experience Boston in comfort and peace.

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!

Lux 2BR Apt w/ Pool and Gym
Welcome to your perfect getaway! Our space combines the comforts of home with luxurious amenities to make your stay truly special. Highlights: ⢠Conveniently close to Downtown Boston ⢠Meticulously deep-cleaned before every stay ⢠Complimentary gourmet coffee, fresh linens, and premium bathroom essentials ⢠24/7 access to a state-of-the-art fitness center ⢠Modern yoga studio and high-tech training equipment ⢠Experience the charm of Somerville while enjoying hotel-quality amenities at home.

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.

Cozy, with Lots of Space
Garden level guest suite in a quiet, single family home. Walk to commuter rail, downtown area, restaurants, and grocery stores. Ideal for an extended stay professional or graduate student seeking a private space. Fully furnished - a separate bedroom (king size bed), living room, bathroom, dining area, and kitchenette (sink, small fridge, microwave - NO STOVE). Includes 2 TVs with streaming service, wi fi, laundry, pool, and a monthly cleaning service. Off street parking.

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/ itâs 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 !

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 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, BBQ, table & chairs you may use.

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.

Courtyard Garden | Pool | BBQ+Fire Tbl | Fireplace
â "Taniaâs place was much more than a placeâŚ.it was a full on fabulous experience." â Courtyard w. lounge + garden â Heated Pool (to 81F)! â Patio w/ Zen fire table* â Natural gas + charcoal grills â Reverse osmosis water filter â 66â smart TV projector â Air filter + purifier: whole house â Central air conditioning â Apple Home pod mini's â Indoor gas fireplace â 300+ Mbps WiFi For non-smokers. No smoking/vaping inside or outside.

Nana-tucket Inn
Charming historic town, home of Brooks School and Phillips Academy, 30 minutes to Boston and Seacoast. Families will enjoy our childrenâs 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!
Popular amenities for Middlesex County rentals with a pool
House rentals with a pool

Elegant & Spacious~Easy Boston Access! STR-25-22

Boston 15 min away.

Beautiful Spacious 4BRM House!

the house of id; vintage shop, accessible space

Shared Hot Tub: Historic Cottage, Walk to Elm Park

Knoll Pocket Park House @ S V

Hidden Gem near Boston w/ Private lake access

Quiet/Private Neighborhood
Other holiday rentals with a pool

Modern and spacious 3Br 3Ba apartment assembly row

3 King Beds 1 Bath Apt w/ Pool

Boston Family Suite: Pool, Gym & Paid Parking

Just Chill'inn Cottage

Private & Comfy New England Guest Suite (I95/I93)

Brand New Luxury Retreat w/ Pool & Fitness Center

Peaceful New England Retreat Close to It All

Elegant 1BR | Harbor & Iconic Boston Skyline Views
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- Hampton Beach
- TD Garden
- Fenway Park
- Boston Common
- Harvard University
- Revere Beach
- Brown University
- New England Aquarium
- Freedom Trail
- MIT Museum
- Boston University
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- Canobie Lake Park
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- Museum of Fine Arts
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- Prudential Center
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- Roxbury Crossing Station
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