Vacation 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.

Guest favorite
Home in Sturbridge
Sturbridge MA 3 BR 2 1/2 Bath Home on Cedar Lake
Fully equipped w/open lake view living space w/gas fpl. Direct access to Lake w/private dock, (2) kayaks, decks, patio, grill & fire pit. Pvt master bed/bath and 2nd bed w/lake view/deck access. Base rate up to 5 people. $50/each add pers-night max 8 total. 4th bed is futon in part finished walkout bsmt/concrete floor. Min 3 night stay pref. Base weekday $315, Weekend $365. Premium rates seasonally/holidays. Local tax added by AirBnB. Ck-out 11 AM, Ck-in 3 PM unless arranged. Sorry no more pets.
May 30 – Jun 6
$305 per night
4.95 out of 5 average rating, 154 reviews
Guest favorite
Home in Woodstock
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.
Dec 26 – Jan 2
$243 per night
4.94 out of 5 average rating, 205 reviews
Guest favorite
Home in Hopkinton
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.
Mar 17 – 24
$129 per night
4.95 out of 5 average rating, 137 reviews

Popular amenities for Worcester County rentals with a pool

House rentals with a pool

Superhost
Home in Marlborough
PrivateRETREAT 4br2ba + Pool + WD + Parking + Wifi
Aug 13 – 20
$350 per night
4.75 out of 5 average rating, 8 reviews
Guest favorite
Home in Brimfield
Luxury Home * Pool * Fireplace
Feb 12 – 19
$914 per night
4.88 out of 5 average rating, 56 reviews
Superhost
Home in Winchendon
Amazing Lakefront Home with Pool- Tatum's Place
Nov 22 – 29
$606 per night
New place to stay
Home in Worcester
Full house in Worcester.
Aug 18 – 25
$99 per night
5.0 out of 5 average rating, 3 reviews
Home in Rutland
Adorable 1 bedroom suite handicap accessible
Feb 19 – 26
$147 per night
4.62 out of 5 average rating, 29 reviews
Home in Uxbridge
Uxbridge Nest
Mar 17 – 24
$115 per night
4.58 out of 5 average rating, 24 reviews
Home in Spencer
Pool Home in country setting
Jan 21 – 28
$529 per night
New place to stay
Home in Millville
Welcome To a Home Away From Home
Apr 3 – 10
$349 per night
New place to stay
Home in Oxford
Spacious Oxford Home w/ Pool - 4 Mi to Lake!
Nov 7 – 14
$369 per night
New place to stay
Superhost
Home in Winchendon
The Perfect Spot at the Lake @ Tatum's Place
Apr 23 – 30
$250 per night
New place to stay

Destinations to explore