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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Guest favorite

Home in Winchendon

4.97 out of 5 average rating, 29 reviews

Amazing Lakefront Home with Pool- Tatum's Place

Bring the whole family to this great place for fun. Escape to our stunning waterfront property on Lake Monomonac! With 200 ft of lake frontage, a sandy beach, private boat docks, pool, it's the perfect year-round getaway. Enjoy spacious living with many bedrooms,4 baths, and TWO kitchens, Infrared SAUNA. Summer fun includes boating, swimming. In the winter, snowmobiling + skiing. Close to many amenities makes it ideal for families. Book now for unforgettable memories at our paradise by the lake!

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, 106 reviews

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]✈

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, 246 reviews

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.

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, 159 reviews

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!

Superhost

A private pool is surrounded by a spacious deck, featuring lounge chairs and shaded seating. Lush greenery borders the area, providing a natural backdrop. The circular pool's clear water reflects the sky, inviting relaxation and enjoyment.

Villa in Charlton

4.76 out of 5 average rating, 70 reviews

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.

Top guest favorite

A cozy living area is featured with a brown sofa adorned with patterned cushions. A small coffee table sits on a patterned rug, and a lamp is positioned beside a side table. In the background, the kitchen is visible, showcasing stainless steel appliances and additional cabinetry.

Guest suite in Hubbardston

4.99 out of 5 average rating, 134 reviews

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.

Superhost

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, 76 reviews

Luxury Home * Pool * Fireplace

This private spacious home sits high on a hill, ringed with trees over looking rolling hills and grazing cattle. Step inside, and be instantly captivated by its natural warmth and glowing ambiance. Just 3 hrs from NYC, 1 hr from Boston, 45 mins. from Hartford and 5 mins. from I90 and I84. Features a sprawling New-England styled front porch. Crystal clear pool nestled in cobblestone paths, lush green grass and whimsical flowers. Modern country charm, vaulted ceilings and open floor plan.

Superhost

A spacious bedroom features a large bed adorned with a patterned green and white quilt. Natural light floods the room through multiple windows, highlighting a small desk and ergonomic chair. Soft lighting is provided by sconces on the walls.

Guesthouse in Worcester

4.77 out of 5 average rating, 57 reviews

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. Enjoy a romantic evening away with our lighted bubble tent hot tub. 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. Pool is a separate rental booked through Swimply. Video tour under “house rules”

Guest favorite

A rectangular pool is framed by a concrete patio, offering a clear view of the water reflecting the sky. Surrounded by greenery, the setting features a welcoming wooden deck area with seating. A shaded structure is positioned nearby, adding to the outdoor space.

Farm stay in Hopkinton

4.95 out of 5 average rating, 133 reviews

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.

Top guest favorite

The image captures a serene outdoor scene at sunset, with vibrant shades of orange and pink illuminating the sky. A fenced pool area is visible in the foreground, while tall trees and stone walls create a natural backdrop, enhancing the tranquil atmosphere.

Apartment in Groton

5 out of 5 average rating, 88 reviews

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.

Guest favorite

Two children stand on a dock overlooking a calm lake. A dog is leashed beside one child. Lush green trees surround the opposite shore, and a distant red-roofed house is visible. The scene conveys a sense of serenity and connection with nature.

Home in Rindge

4.94 out of 5 average rating, 33 reviews

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.

Guest favorite

A well-maintained backyard pool area features a sparkling blue pool surrounded by vibrant green artificial grass. Lounge chairs with striped fabric offer comfortable seating, and inflatable pool toys add a playful touch. A shaded area with a red umbrella enhances outdoor relaxation.

Apartment in Fitchburg

5 out of 5 average rating, 28 reviews

Relaxing Getaway With a Pool

Welcome to our charming 1-bed, 1-bath side-by-side unit, a perfect paradise with a pool. My husband and I, along with our cat, Mia, live in the main house. Enjoy the TVs in both the living room and bedroom, each offering streaming options, along with a fully equipped kitchen. The futon converts into a full-size bed for additional guests. It’s a great place to unwind. We look forward to hosting you! *Pool closure Labor Day weekend 9/1/25