
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.
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House rentals with a pool

Home in Worcester
4.83 out of 5 average rating, 6 reviewsFull house in Worcester.
ElizabethRating, 5 stars14 months ago
Albert was an accommodating host. His place had everything we needed. It was an easy, comfortable stay for a very reasonable price!
Guest favorite

Home in Hopkinton
4.95 out of 5 average rating, 155 reviewsHopkinton Mass 3+ Bedrooms - Great location!
DeanneRating, 5 stars1 week ago
Brad was very friendly and helpful. Beautiful home!
Superhost

Home in Winchendon
4.96 out of 5 average rating, 26 reviewsAmazing Lakefront Home with Pool- Tatum's Place
ShawnRating, 5 stars2 days ago
This property and experience was everything and more! From the location on the beautiful lake to the clean bedrooms and common rooms! Plenty of space to entertain everything was clean and modern! The hostess Ashley was very attentive to any questions I had and very friendly! Some places I’ll never return to because of the host. I shall be raving about this place for years to come with memories to accompany them! 10/10 experience for sure!
Guest favorite

Home in Worcester
4.96 out of 5 average rating, 101 reviewsCourtyard Garden | Pool | BBQ+Fire Tbl | Fireplace
XufengRating, 5 stars3 weeks ago
From the moment we arrived, we felt completely at home thanks to the incredibly warm and welcoming hosts, Tania and Glenn. They went above and beyond to make our stay comfortable, offering great local tips and always greeting us with a smile. Their hospitality truly made a difference. The home itself is absolutely stunning—beautifully designed, impeccably clean, and filled with thoughtful touches that made it feel extra special. Whether we were enjoying a quiet morning coffee or relaxing in the cozy living area after a day of exploring, everything was perfect. This was one of the best Airbnb experiences we've ever had. If you're lucky enough to find availability here—book it! You won't regret it. Thank you, Tania and Glenn, for a truly unforgettable stay! 💛
Guest favorite

Home in Woodstock
4.94 out of 5 average rating, 239 reviewsCedar Ridge: House or House+Apartment
AlissaRating, 5 stars1 week ago
We LOVED: 1) The location! The driveway is long & sand/gravel but you could drive it in a sedan fine. 2) The amenities! The pack n play was a HUGE lifesaver! 3) This location is mostly child friendly. 4) The view is phenomenal! When we woke up & opened the curtains for the first time, we were in awe! 5) The host was extremely helpful. The hot water went out once, but she was over in 5 minutes to fix it. Some feedback: 1) The windows in the ceiling in the master bed! They're HUGE and BRIGHT. 2) The bugs. Ants. Spiders. It was a struggle. NOW I WILL SAY - I brought this up to the host on day 3 and they were more than willing to come help how they could. The house is located in the middle of the forest, but it was a lot. If it weren't for an m&m left under the nightstand in the bedroom by a previous guest, it probably wouldn't have been so bad. 3) the coffee maker was pretty rough when we got there.. a simple over site by the crew. Overall, I would definitely consider this location again
Superhost

Home in Winchendon
4.75 out of 5 average rating, 4 reviewsThe Perfect Spot at the Lake @ Tatum's Place
AshleyRating, 5 stars4 months ago
Great stay! House was clean and spacious for our party of 8. We had everything we needed for our weekend stay in January. We traveled with our twin 18 month olds and had access to playpens and a high chair for which I was very grateful! They even had some books and legos for the kids to play with!

Home in Worcester
4.78 out of 5 average rating, 32 reviewsBeautiful & Historic Cottage, Steps to Elm Park
AmyRating, 5 stars1 month ago
location was easy to find in a nice residential area just outside of the city, very clean, owner responded quickly to messages
Guest favorite

Home in Brimfield
4.88 out of 5 average rating, 73 reviewsLuxury Home * Pool * Fireplace
DanaRating, 5 stars4 months ago
We had a very nice stay for a family wedding. Sharing the house with two combined families in January and the house was great for this. There are rooms with 3-4 beds in each so if you are looking for bedroom privacy then this house probably isn’t it. That said, we are all family so was fun to bunk up! The area is beautiful and there r a great set of trails right at the end of the road for hiking, walking cross country skiiing etc. Overall, a great stay and Kimberly was very communicative with everything
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- Boston Common
- Fenway Park
- Revere Beach
- TD Garden
- Harvard University
- Lynn Beach
- Brown University
- Six Flags New England
- New England Aquarium
- Monadnock State Park
- Faneuil Hall Marketplace
- Freedom Trail
- Canobie Lake Park
- Prudential Center
- Roger Williams Park Zoo
- MIT Museum
- Museum of Fine Arts, Boston
- Quincy Market
- Bunker Hill Monument
- Pawtucket Country Club
- Isabella Stewart Gardner Museum
- Boston Public Library
- Symphony Hall
- Brimfield State Forest