
Holiday rentals with a pool in Milford
Find and book unique homes with a pool on Airbnb
Quick stats about holiday rentals with a pool in Milford

Total holiday rentals
Explore 20 holiday rentals in Milford

Nightly prices starting at
Milford holiday rentals start at €60 per night before taxes and fees

Verified guest reviews
Over 60 verified reviews to help you choose

Pet-friendly holiday rentals
Find 20 rentals that welcome pets

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wifi availability
20 of Milford holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Milford rentals
Top-rated rentals with a pool in Milford
Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

Rustic Farmette Studio w/yearround Hot Tub
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, or a family with a young kid. Please include all individuals (&pets) in your booking.

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

In-law Apartment, Full Kitchen, Near Mt Wachusetts
Your home away from home is a spacious & newly renovated basement/in-law apartment (approx 1100 sq feet) located below the main house, with its own private entrance, dedicated parking & in walkable neighborhood. The unit has a bathroom, full kitchen, living room & bedroom w/queen bed & extra tv. Hubbardston is a quaint little town with no stop-lights yet conveniently located to many beautiful hiking trails, fishing spots and lakes. 10 minutes from route 2 and 15 minutes from Mt Wachusetts.

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.

Get comfy in the country!
This special place is close to everything, making it easy to plan your visit. Just 10 minutes away from town. Secluded cabin on a 57-acre farm outlooking a large paddock with 4 highland cows. This beautiful property has a neighboring golf course and trails connecting to Heritage Park. Pool. Fireplace. Amazing sunsets! Who wouldn’t want to live like Yellowstone for a little? Home of Welcome Pastures, a Nonprofit 501(c)3 organization. Portion of proceeds go towards the foundation.

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 !

Artist studio in the woods
Take it easy at this unique and tranquil getaway. Be a little bohemian, stay in an artist’s studio for two adults, views of woods and stone walls.walk along a 300 stone wall past a 5000 gallon koi pond, and discover a stone sculpture in the woods. Wall of windows, private deck, queen size bed, kitchenette, full bath, dishwasher, Wi-Fi, cable tv, guest robes, iron and board, kuerig, all necessary utensils. Quiet, tranquil, relax. 47 minutes from Gillette Stadium.

Great country getaway
Quiet country 1895 victorian living.House is in a small neighborhood on a main road across from a cemetery. All bedrooms are located on the 2nd floor, may not be suitable for those with mobility issues,family owned wineries nearby and a micro brewery. 20 min to major highway. Small downtown village area with restaurants and groceries. 30 min from Bryant University and about one hour from Newport, Boston and beaches. Hosts live two houses away

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.
Popular amenities for Milford rentals with a pool
House rentals with a pool

Cedar Ridge: House

Private Heated Pool • Upscale 4BR • 13 min 2 Beach

The Secret Garden 4 Bedroom, 7 Bed 3 Baths

Nature's Nook

Cozy Barrington Home with a Private Pool

Spacious vacation unit in premium suburban town

Edgewater Retreat | Oceanfront Home | Heated Pool

Luxury Boston Ranch –Sleeps 8|Pet+|Heated pool
Apartment rentals with a pool

Villa Flora @ Norwich Inn & Spa

Spa Dreams

“Luxury 2BR Cambridge | Pool + Parking”

Mohegan Sun Retreat: Pool•Hot Tub•Near Norwich Spa

Back Bay Hub for Red Sox & Fall Campus Trips
Other holiday rentals with a pool

Country Cottage in the City

Pool Is Open in Sept! Steps from Harbor + Old Town

Farmhouse Guest Apartment

Amazing studio

Charming 2-story private Guesthouse

Cozy Private Studio Unit w/ Laundry and Parking!

Cozy private apt 8 mins from UCONN - solar powered

Rustic Cabin | 25 Min (16 Mi) to Gillette Stadium
Destinations to explore
- Fenway Park
- Harvard University
- TD Garden
- Boston Seaport
- Gillette Stadium
- Boston Common
- Revere Beach
- Boston University
- Boston Convention and Exhibition Center
- Freedom Trail
- New England Aquarium
- Bonnet Shores Beach
- Boston College
- Canobie Lake Park
- Northeastern University
- Duxbury Beach
- MIT Museum
- Tufts University
- Harvard Square
- Quincy Market
- Easton Beach
- Saquish Beach
- Massachusetts Institute of Technology
- Roger Williams Park Zoo





