Vacation 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.

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Guest favorite

Rental unit in Waltham

4.97 out of 5 average rating, 264 reviews

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 will love this large 400 sq. ft private 1 bedroom studio. This unit has a private 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)

Guest favorite

Villa in Newton

4.93 out of 5 average rating, 56 reviews

Explore Boston in style! Dream home, pool, sauna.

Relax in this calm, elegant lovely home with fully equipped high-end kitchen, 4 modern bathrooms, private fenced garden with hot tub and cold pool. Conveniently located in South Newton - one of the most desirable and safe suburbs of Boston. 3 minutes walk to a temple, 15-20 minutes drive to downtown Boston, 8 minutes drive to BC, 20 minutes drive to Babson, Bentley, Harvard & MIT. 25 minutes walk to a T (Green line "Newton Highlands"). Great restaurants and shopping areas within minutes drive.

Guest favorite

Guesthouse in Maynard

5 out of 5 average rating, 26 reviews

Cute mill house: 3BR•Wood stove *Brkfst included*

Welcome to the most walkable town in Metro Boston, w/ movie theater, live performance venue, beer garden, galleries, shops, & 17 restaurants 1/2mi from our front door. Our 1910 mill town company house is a little oasis. This is a two-family house; two separate private residences side-by-side. My family occupies the other side. Between house & garage, the outside dining area and fire pit are for your private use. Beyond the garage, we invite you to share our backyard w/ pool and badminton.

Guest favorite

Home in Hopkinton

4.94 out of 5 average rating, 144 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.

Guest favorite

Rental unit in Groton

5 out of 5 average rating, 68 reviews

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.

Guest favorite

Rental unit in Holliston

4.96 out of 5 average rating, 119 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.

Superhost

Rental unit in Fitchburg

5 out of 5 average rating, 14 reviews

Relaxing Cozy Getaway

Welcome to our cozy 1-bedroom, 1-bathroom side-by-side unit, a perfect poolside paradise during the warmer months! My husband and I, along with our cat, Mia, live in the main house. Enjoy the TVs in both the living room and bedroom, along with a fully equipped kitchen. The futon converts into a full-size bed for additional guests. It’s a great place to relax, whether indoors or by the firepit making s'mores. We look forward to hosting you!

Guest favorite

Home in North Andover

4.95 out of 5 average rating, 149 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!

Guest favorite

Townhouse in Groton

5 out of 5 average rating, 66 reviews

Potager Farm Private Townhouse

Whether to attend a concert at Groton Hill Music, a wedding at Gibbet Hill, or to visit your students at Lawrence Academy and the Groton School, Potager farm is your conveniently located home away from home. Potager was built over a period of many years beginning in the late 1700's and has been lovingly restored. There is a Rail Trail & State Forest within walking distance. Kayaking 1 mile.

Superhost

Rental unit in Boston

4.8 out of 5 average rating, 30 reviews

Spacious suite in Boston near BC & Harvard

Experience Boston in this beautiful renovated chapel apartment complex fully equipped for your comfortable stay! Unit Features -> 24/7 Concierge -> Blazing Fast WiFi -> 55” Smart TV -> Fully Stocked Kitchen -> Washer & Dryer -> Comfortable Queen Bed Ideal for business travelers, couples, nurses, and everyone looking to experience Boston in style!

Guest favorite

Guest suite in Burlington

4.96 out of 5 average rating, 28 reviews

Stay a While, Studio Apartment-Pet Friendly

Welcome to our fabulous boho chic studio apartment, located 25 minutes North of Boston. We welcome all guests, including your beloved pets! 3/4 of a mile to the nearest MBTA bus stop, 3 miles to Lahey and 6 miles to Winchester Hospital. And best of all, Dunkin Donuts is a 5 minute walk from us ;)

Guest favorite

Guesthouse in Dedham

4.95 out of 5 average rating, 191 reviews

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. Besides the pool, there are two garden ponds where we keep decorative fish, and a regular parade of various types of birds and even wild turkeys and deer.