Vacation rentals with a pool in Worcester County

Find and book unique homes with a pool on Airbnb

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Popular amenities for Worcester County rentals with a pool

House rentals with a pool

The spacious living and dining area features a light-colored sofa, a wooden coffee table, and a dining table surrounded by chairs. Soft lighting enhances the open layout, creating a relaxed ambiance. A large painting and decorative elements are also visible in the surroundings.
Home in Worcester
4.83 out of 5 average rating, 6 reviews

Full 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
An outdoor swimming pool is surrounded by a spacious patio and lush greenery. Sun loungers are arranged around the pool, with a shaded seating area nearby. The house features a multi-level deck overlooking the pool, creating a relaxing outdoor space for guests.
Home in Hopkinton
4.95 out of 5 average rating, 155 reviews

Hopkinton 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 reviews

Amazing 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
A clear blue pool reflects the surrounding area, framed by a patio with lounge chairs. A shaded seating area is visible next to the pool, enhancing outdoor relaxation options.
Home in Worcester
4.96 out of 5 average rating, 101 reviews

Courtyard 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
A serene swimming pool is surrounded by well-maintained greenery, with lounge chairs placed along the deck. Large blue umbrellas provide shade, enhancing the outdoor space suitable for relaxation. A stone wall borders the area, adding a natural touch.
Home in Woodstock
4.94 out of 5 average rating, 239 reviews

Cedar 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
A light-filled living area features a comfortable sectional sofa, two accented chairs, and a wooden sideboard. A large television is mounted on the wall opposite the seating. Windows allow natural light to fill the space, enhancing the cozy ambiance.
Home in Winchendon
4.75 out of 5 average rating, 4 reviews

The 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!
A serene outdoor area features a blue saltwater pool surrounded by brick pavements and lush greenery. The space is complemented by a cozy seating arrangement and French doors leading into the carriage house, creating an inviting atmosphere for relaxation.
Home in Worcester
4.78 out of 5 average rating, 32 reviews

Beautiful & 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
The outdoor space features a landscaped yard with vibrant flowers and neatly arranged cobblestone paths. A crystal-clear pool is visible beyond a decorative black fence, surrounded by trees and greenery. A gazebo adds character to the serene environment, ideal for relaxation.
Home in Brimfield
4.88 out of 5 average rating, 73 reviews

Luxury 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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