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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Superhost

A large, inviting pool is surrounded by a neatly landscaped yard featuring an array of lounge chairs. A wooden cabana is situated nearby, and expansive views of the lake and trees are visible in the background under a clear blue sky.

Home in Winchendon

4.91 out of 5 average rating, 35 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!

Top guest favorite

An outdoor lounge area features a circular table surrounded by curved sofas adorned with cushions. Soft curtains frame the space, while potted flowers add vibrant color. Natural light filters through the overhead structure, creating a relaxed atmosphere for gatherings.

Home in Worcester

4.96 out of 5 average rating, 110 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

The renovated house is situated amidst lush greenery, surrounded by trees and a well-maintained lawn. A small swimming pool is visible within a fenced area, complemented by several umbrellas for shade, enhancing the outdoor ambiance on a sunny day.

Home in Woodstock

4.94 out of 5 average rating, 254 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.

Top 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, 161 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!

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, 151 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.

Home in Brimfield

4.87 out of 5 average rating, 78 reviews

Country Holiday Retreat * 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.

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

4.82 out of 5 average rating, 39 reviews

Beautiful & Historic Cottage, Steps to Elm Park

A true hidden gem, this 2-bed, 2-bath vacation rental boasts a unique historic background and a quiet, idyllic location. Make yourself at home in the tastefully furnished mid-century interior or relax poolside surrounded by lush greenery. Choose to explore Elm Park, try out local restaurants, or wander Worcester Common — all located within walking distance. Regardless of your plans, you'll love coming home to this peaceful carriage house on one of the most beautiful streets in Worcester!

Superhost

A decorative sign hangs from a post, displaying the name 'Ellen Elizabeth Estates' along with the establishment year, 1956. The sign is surrounded by lush greenery, visible in the background, which enhances the inviting exterior of the property.

Apartment in Millbury

4.5 out of 5 average rating, 6 reviews

Ellen Elizabeth Estates - The Kristen Leigh Apt.

✨ Restored 1956 Estate ✨ Original swirl ceilings, golden, warmth, hardwood floors, and mid-century charm — lovingly preserved with modern comfort. A rare stay where history meets home. * Full kitchen, full bathroom, dining room , • The Swirl Ceiling Room – to showcase that rare craftsmanship living room, beautiful Queen size bed , solid oak headboard - classic - baseboard New England charm, assigned parking, quick wifi Long term rentals are welcomed! Total New England Flare!

Guest favorite

A historic stone farmhouse is set on a spacious green lawn, complemented by a vibrant red barn in the background. Tall trees provide shade, and a carefully arranged stone border outlines the lush garden area, creating a tranquil outdoor setting.

Farm stay in Hopkinton

4.96 out of 5 average rating, 141 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

A spacious exterior view showcases a two-story light gray house with a brick chimney, set against a backdrop of lush greenery and a mix of trees. A charming barn is visible in the distance, complementing the well-maintained gardens and open lawn.

Apartment in Groton

5 out of 5 average rating, 92 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

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

4.81 out of 5 average rating, 70 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. 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. Hot tub is included and available for use until late October. Pool is a separate rental and closed for the season.

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

4.95 out of 5 average rating, 37 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.