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

Home in Worcester
4.83 out of 5 average rating, 6 reviewsFull house in Worcester.
Top Guest favourite

Home in Hopkinton
4.95 out of 5 average rating, 160 reviewsHopkinton Mass 3+ Bedrooms - Great location!
Superhost

Home in Winchendon
4.93 out of 5 average rating, 30 reviewsAmazing Lakefront Home with Pool- Tatum's Place
Top Guest favourite

Home in Worcester
4.96 out of 5 average rating, 107 reviewsCourtyard Garden | Pool | BBQ+Fire Tbl | Fireplace
Guest favourite

Home in Woodstock
4.94 out of 5 average rating, 250 reviewsCedar Ridge: House or House+Apartment
Superhost

Home in Winchendon
4.75 out of 5 average rating, 4 reviewsThe Perfect Spot at the Lake @ Tatum's Place

Home in Worcester
4.8 out of 5 average rating, 35 reviewsBeautiful & Historic Cottage, Steps to Elm Park
Superhost

Home in Brimfield
4.87 out of 5 average rating, 77 reviewsLuxury Home * Pool * Fireplace
Other holiday rentals with a pool
Top Guest favourite

Home in Hopkinton
4.95 out of 5 average rating, 160 reviewsHopkinton Mass 3+ Bedrooms - Great location!
Top Guest favourite

Home in Worcester
4.96 out of 5 average rating, 107 reviewsCourtyard Garden | Pool | BBQ+Fire Tbl | Fireplace
Guest favourite

Home in Woodstock
4.94 out of 5 average rating, 250 reviewsCedar Ridge: House or House+Apartment
Guest favourite

Cabin in Hubbardston
4.94 out of 5 average rating, 162 reviewsTriggers Cabin
Guest favourite

Campervan/RV in Hubbardston
4.94 out of 5 average rating, 86 reviewsHooties Hollow
Superhost

Campervan/RV in Hubbardston
4.87 out of 5 average rating, 23 reviewsFoxey's
Guest favourite

Apartment in Fitchburg
5 out of 5 average rating, 31 reviewsRelaxing Getaway
Top Guest favourite

Guest suite in Hubbardston
4.99 out of 5 average rating, 140 reviewsIn-law Apartment, Full Kitchen, Near Mt Wachusetts
Destinations to explore
- Farmstay rentals Worcester County
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- Rentals with a fireplace Worcester County
- Rentals with a patio Worcester County
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- Apartment rentals Worcester County
- Rentals with a fire pit Worcester County
- Rentals with outdoor seating Worcester County
- Condo rentals Worcester County
- Rentals with a washing machine and dryer Worcester County
- Rentals with beach access Worcester County
- Fitness-friendly rentals Worcester County
- Rentals with pools Massachusetts
- Rentals with pools United States
- Fenway Park
- Boston Common
- TD Garden
- Revere Beach
- Harvard University
- Brown University
- Lynn Beach
- Six Flags New England
- New England Aquarium
- Canobie Lake Park
- Monadnock State Park
- Freedom Trail
- Faneuil Hall Marketplace
- MIT Museum
- Quincy Market
- Museum of Fine Arts, Boston
- Prudential Center
- Roger Williams Park Zoo
- Boston Children's Museum
- Blue Hills Ski Area
- Franklin Park Zoo
- Bunker Hill Monument
- Brimfield State Forest
- Isabella Stewart Gardner Museum