Vacation rentals with a pool in Milford

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Milford

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

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Guest favorite

Apartment in Waltham

4.98 out of 5 average rating, 210 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)

Dec 12 – 19

G$26,067 GYD per night

Guest favorite

Apartment in Norwich

4.9 out of 5 average rating, 231 reviews

Cozy Stay w Pool 4 mi to Mohegan, 7 mi to Foxwoods

THE POOL IS OPEN AS OF MAY 1st! Welcome to our charming 2-bedroom apartment. This centrally located spot is the perfect getaway to escape the hustle and bustle of the big city and enjoy a more relaxed pace of life. The unit comes in at a spacious 950 sq ft - ideally suited for couples, solo travelers, families and can comfortably accommodate up to 4 people. Feel free to use the grill of course, but you may have to fill the propane tank. You can do so at the Walmart which is 12 minutes away!

Oct 2 – 9

G$21,264 GYD per night

Superhost

Guest suite in Beverly

4.85 out of 5 average rating, 662 reviews

Historic North Shore, private suite & bathroom

Minutes from Salem! Relax in historic Beverly (walk to Beverly shops) in your private suite; bedroom, living room, and small bathroom, connected to our home, but private entrance. Just minutes from Salem. Commuter line to Boston and close to beautiful North Shore beaches and historic sites. Beaches within biking and driving distances, downtown, parks, hiking. Comfy, soft king bed, queen pull out couch, and plenty of linens. Great for couples, solo adventurers, business travelers, and families.

Aug 30 – Sep 6

G$25,701 GYD per night

Guest favorite

Apartment in Bristol

4.96 out of 5 average rating, 135 reviews

Cozy, Peaceful One Bedroom Apartment in Bristol

Cozy peaceful one bedroom apartment centrally located in picturesque Bristol. Located on a dead end street. Just a 20 minute walk to downtown, Colt State Park and waterfront. Centrally located between Providence and Newport and Boston and the Cape. Enjoy amenities such as; pool, private deck, espresso and tea bar, and Netflix . Enjoy all Bristol has to offer: museums, Saturday market, fantastic restaurants, boating, beach, quaint shops and of course the oldest continuous 4th of July Parade!

Jan 22 – 29

G$24,558 GYD per night

Guest favorite

Condo in Norwich

4.99 out of 5 average rating, 112 reviews

Peaceful Oasis steps from Mohegan Sun

Feel at home at our contemporary yet cozy villa. A private and quiet space in the heart of the area's local attractions (walkable to Mohegan Sun/short drive to Foxwoods). Perfect for a fun-filled weekend or a simple and quiet getaway. Enjoy the scenic views of the surrounding golf course or indulge at the on-site renowned spa. Other noteworthy amenities include a year round opened clubhouse, sauna, and hot tub as well as two beautiful seasonally opened pools. This unit comfortably sleeps 4.

Jan 10 – 17

G$29,844 GYD per night

Guest favorite

Farm stay in Thompson

4.99 out of 5 average rating, 133 reviews

Rustic Farmette Studio w/ Hot Tub & seasonal pool

Relax and rejuvenate at this unique getaway on 20 acres in CT’s Quiet Corner. Just an hour from Boston, Providence, & Hartford, enjoy this private in-law studio with beautiful forest views. Lounge in bath robes & soak in the hot tub, take a walk along the trails, enjoy local vineyards, or explore antiques. Folks from all backgrounds and identities are welcome at The Farmette. Ideal for couples, solo travelers, a small family. Please include all individuals (&pets) in your booking.

Oct 10 – 17

G$40,032 GYD per night

Guest favorite

Home in Woodstock

4.93 out of 5 average rating, 209 reviews

Cedar Ridge

In Connecticut's "Quiet Corner", a fully renovated 2-level house bathed in sunlight, with lovely flower beds and stunning hilltop views. Relax on its patios and in its small swimming pool, stroll along its forest paths, observe birds (including birds of prey) and other wildlife. New England's "Last Green Valley National Heritage Corridor" offers multiple attractions and is home to many schools, universities, fairs, artists/artisans, farms, special events and year-round activities.

Apr 16 – 23

G$58,610 GYD per night

Guest favorite

Guest suite in North Smithfield

4.94 out of 5 average rating, 108 reviews

*Country style 2 Bedroom Pet Friendly Guest Suite*

Bring the whole family to this countryside Mini Resort with lots of room for fun. Pet friendly, spacious 2 bedroom, tv in both, full applianced kitchen, bathroom with handicapped shower, washer & dryer. Dining room with coffee station, gorgeous living room with access to a bright sun room overlooking the patio and the large all fenced in yard with pool and fire pit. Separate entrance, with no steps, parking for 3 cars. 1 minute from the highway! 10 minutes from Bryant University.

Sep 10 – 17

G$35,033 GYD per night

Guest favorite

Home in Middleborough

4.94 out of 5 average rating, 296 reviews

Private retreat setting on 4 acres 1

Gatherings, parties, events, reunions, etc. with 8 or more total sleepers /non sleepers MUST be discussed prior to booking. A 5 minutes from Rte. 495, secluded, 2 bedroom 1200 sq.ft. apartment. Amenities include -- in-ground pool, horseshoe pits, tennis/basketball court, fully lit for night time use. Central air, full bath, eat in kitchen, Juliet balcony, private drive & entrances, 2 HD flat screen TV"s, Netflix, On Demand WIFI. Very comfortable for two or a couple with children.

Apr 7 – 14

G$21,071 GYD per night

Guest favorite

Guesthouse in North Andover

4.97 out of 5 average rating, 186 reviews

Spacious Studio Guesthouse at Winery w/ Tasting

*A North Shore Favorite!* This former art studio is breathtakingly beautiful and is a true getaway to relax and feel at peace. It has great lighting and is located directly off of one of our historic barns. The space is perfect for a romantic retreat or the traveling professional looking for a place to call their home away from home. Located in an affluent neighborhood, minutes away from shopping and restaurants. Booking includes a wine tasting and 10% off all wine purchases!

Sep 16 – 23

G$86,764 GYD per night

Guest favorite

Home in Hopkinton

4.95 out of 5 average rating, 138 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.

G$28,361 GYD per night

Guest favorite

Guest suite in Brooklyn

4.92 out of 5 average rating, 153 reviews

Affordable In-Law Apartment in Brooklyn, CT

This is a great in-law style apartment which was fully renovated in 2020. It can be booked for short stays or more lengthy visits to Northeast CT. The apartment is one minute from Scenic route 169 and Route 6. It is 30 minutes to UCONN and ECSU. We are close toThe Pomfret School/Rectory School. It is 35 mins to Mohegan Sun and Foxwoods. My place is rural and peaceful. It is good for couples, solo adventurers, business travelers, and families.

Apr 18 – 25

G$15,399 GYD per night