
Vacation rentals with a pool in Worcester County
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Top-rated rentals with a pool in Worcester County
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

Courtyard Garden | Pool | BBQ+Fire Tbl | Fireplace
★ "Tania’s place was much more then a place….it was a full on fabulous experience." ☞ Courtyard w. lounge + garden ☞ Pool! ☞ Patio w/ Zen fire table* ☞ Natural gas + charcoal grills ☞ Reverse osmosis water filter ☞ 66” smart TV projector ☞ Air filter + purifier: whole house ☞ Central air conditioning ☞ Apple Home pod mini's ☞ Indoor gas fireplace ☞ 300+ Mbps WiFi For non-smokers. No smoking inside or outside. 8 mins → DT Worcester (shops, dining) 17 mins → Worcester Regional Airport [ORH]✈

Cedar Ridge: House or House+Apartment
2 OPTIONS: HOUSE or HOUSE+APARTMENT In CT’s Quiet Corner: renovated 2-level house bathed in light, with nice 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.

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!

Summer Home near TreeHouse Brewery | Private Pool
Bring the whole family to this lovely villa with lots of free parking and multiple comfy King Beds. This Villa seats on 1 Acre in a really residential and quiet neighborhood in Charlton MA. The property boasts of a spacious backyard with a private play ground for kids and a private pool with a large deck. It's less than 10 minutes away from the Treehouse brewery. The Heritage Country Club golf course is about 10 minutes from the Villa. There are several lakes within 20 minutes from the Villa.

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.

The Perfect Spot at the Lake @ Tatum's Place
Bring the whole family to this great place with lots of room for fun. It has 3 very spacious bedrooms and 3 full bathrooms. Shared laundry room. Lots of space to entertain and a beautiful view of Lake Monomonac. It has 200ft of lake frontage and a large back yard. This is available November- April. In the winter, enjoy ice fishing, snowmobiling + skiing . Close to many amenities makes it ideal for families. Book now and experience unforgettable memories at our paradise by the lake!

Ellen Elizabeth Estates - The Kristen Leigh Apt.
✨ Restored 1956 Estate ✨ Original swirl ceilings, golden, warmth, hardwood floors, and mid-century charm — lovingly preserved with modern comfort. A rare stay where history meets home. * Full kitchen, full bathroom, dining room , • The Swirl Ceiling Room – to showcase that rare craftsmanship living room, beautiful Queen size bed , solid oak headboard - classic - baseboard New England charm, assigned parking, quick wifi Long term rentals are welcomed! Total New England Flare!

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.

Barn in Ashby
guest suite in attached barn. 1 queen sized bed. Large couch with pull out footrest NO KITCHEN. There IS a Coffee machine, Microwave, & mini fridge in your suite. wifi and chromecast TV. Elliptical machine in the barn basement. There is no kitchen in this unit. By Car: 6 minutes to Mount Watatic state park 11 minutes to Fitchburg State University 13 minutes to Cushing Academy 13 minutes to Fitchburg Commuter Rail station 19 minutes to Franklin Pearce University

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.

Quiet Oasis In The City
Forget your worries in this spacious and serene space. We are right in the city but you'll feel miles away. This two level guest home is surrounded by nature and very relaxing. Two bedrooms and two baths. Two king sized beds. One full bath with oversized tub downstairs. Upstairs bath with standing shower. Full kitchen and coffee and tea. Hot tub is included and available for use until late October. Pool is a separate rental and closed for the season.

The Shoreline
Welcome to The Shoreline. This Classic New England Lakehouse is located on Lake Monomonac, minutes away from amenities but tucked away in small town America. This property is the ideal getaway for a relaxing peaceful vacation. The kitchen and living areas are comfortable and clean, but the real star is the lake itself—perfect for boating, kayaking, swimming, and fishing. Enjoy the 180 degree water views and over 600 ft of beautiful shoreline.
Popular amenities for Worcester County rentals with a pool
House rentals with a pool

Hopkinton Mass 3+ Bedrooms - Great location!

Courtyard Garden | Pool | BBQ+Fire Tbl | Fireplace

Cedar Ridge: House or House+Apartment

The Shoreline

Spacious Oxford Home w/ Pool - 4 Mi to Lake!

The Perfect Spot at the Lake @ Tatum's Place

Beautiful & Historic Cottage, Steps to Elm Park

Country Holiday Retreat * Pool * Fireplace
Other vacation rentals with a pool

Hopkinton Mass 3+ Bedrooms - Great location!

Courtyard Garden | Pool | BBQ+Fire Tbl | Fireplace

Cedar Ridge: House or House+Apartment

Triggers Cabin

Ellen Elizabeth Estates - The Kristen Leigh Apt.

Barn in Ashby

Relaxing Getaway

In-law Apartment, Full Kitchen, Near Mt Wachusetts
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- Fenway Park
- Boston Common
- TD Garden
- Harvard University
- Revere Beach
- Brown University
- Six Flags New England
- Lynn Beach
- New England Aquarium
- Monadnock State Park
- Canobie Lake Park
- MIT Museum
- Freedom Trail
- Faneuil Hall Marketplace
- Museum of Fine Arts, Boston
- Quincy Market
- Prudential Center
- Roger Williams Park Zoo
- Franklin Park Zoo
- Boston Children's Museum
- Bunker Hill Monument
- Symphony Hall
- Isabella Stewart Gardner Museum
- Brimfield State Forest