Holiday 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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Top guest favourite

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

Gather, Cook & Unwind, 3BR, Fireplace

A private resort — without leaving Worcester. Heated pool, fire table, garden courtyard … your own enclosed escape. ★ "Tania’s place was much more than a place….it was a full on fabulous experience." 🏊Heated Pool (to 81F) 🌿 Courtyard w. lounge + garden 🔥Patio w/ Zen fire table* 🍽️ Natural gas + charcoal grills 💧 Reverse osmosis water filter 66” smart TV projector ❄️ Central air conditioning 🔥Indoor gas fireplace 📶300+ Mbps WiFi For non-smokers. No smoking/vaping inside or outside.

4.97 out of 5 average rating, 132 reviews

Guest favourite

A spacious yard is surrounded by tall trees, showcasing a playground with a slide and swings. A garden area is interspersed with colorful flowers and is set against the backdrop of lush greenery. A trampoline is visible in the distance, along with a greenhouse.

Farm stay in Rutland

Farm Living

We offer a quiet country setting on a small working farm, with cows, horses, pigs, goats, donkeys, peacocks, emu, rabbits, dogs, chickens, ducks and wildlife strolling now and then. There’s opportunity to interact with the animals. Pack n play available for little ones upon request and another twin fold up bed. We truly want all of our guest to enjoy all the farm has to offer and enjoy the peacefulness. Please inquire about kayak rentals. We also have a game room available to rent. See photos

4.95 out of 5 average rating, 425 reviews

Guest favourite

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

Shared Hot Tub: Historic Cottage, Walk to Elm Park

Walk to Shops & Restaurants | Convenient Rail Access to Boston & Fenway Park A true hidden gem, this vacation rental offers hassle-free access to Boston's top sights without the stress of city driving or paid parking. Worcester’s Union Station makes it easy to hop on the MBTA — leave the car parked and adventure, then return to the comfort of Worcester at the end of the day. The home is ideal for sports fans, culture lovers, and those who want big-city access with suburban peace. Book today!

4.81 out of 5 average rating, 64 reviews

Guest favourite

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

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 5 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!

4.89 out of 5 average rating, 54 reviews

Villa in Charlton

Fall & Winter Home Escape Near Tree House Brewery

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.

4.64 out of 5 average rating, 85 reviews

Top guest favourite

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

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.

4.98 out of 5 average rating, 228 reviews

Top guest favourite

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

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 4 futons/mattresses. 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!

4.95 out of 5 average rating, 180 reviews

Guest suite in Rutland

Cozy house in Rutland MA 3 beds and 1 office space

Family-Friendly Getaway Unwind in this cozy, nature-filled escape Car Rentals 2017 Porsche Macan Living Room with a 85" TV/ Electric Fireplace 1) Master bedroom King size bed 75" TV 2) 2 Queen size beds each bedroom has a 65" TV Boat /Kayak rental during summer is perfect for families and friends to enjoy fishing and relaxing time. Nestled in a serene, woodsy setting, our home offers, relaxation, a firepit for cozy nights, and easy access to nearby attractions. Perfect to relax.

4.78 out of 5 average rating, 9 reviews

Superhost

The Kristen Leigh bedroom features a wooden bed frame with an intricately designed headboard. A bedside lamp provides soft lighting. A mirror reflects the room, while a door leads to a cozy space. Neutral tones and patterned bedding enhance the inviting atmosphere.

Flat in Millbury

Ellen Elizabeth Estates - The Kristen Leigh Apt.

Please ask if interested in long term discounts being offered . ✨ 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

4.57 out of 5 average rating, 7 reviews

Top guest favourite

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

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.

4.96 out of 5 average rating, 166 reviews

Guest favourite

Home in Sterling

Pool•1000mbpsWiFi•DeepTub•Fireplace•Full Kitchen

Welcome to Echo Point™️ Luxury Home 15min drive to Wachusett Mountain [The Space] Amenities and services → large 40x20 Pool (memorial day-9/1)SemiPrivate → Well-equipped kitchen → King Bed | Queen Bed | 2 Full beds → AC in all main rooms (memorial day-9/1) → Netflix/Roku → 6 seat Dining → On-Site Parking → Garden patio → Prep Vanity Add my listing to your Wishlist by clicking the ❤️ in the upper-right corner. Entire space is included in this rental. Please, make yourself at home.

4.87 out of 5 average rating, 30 reviews

Guest favourite

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

Cedar Ridge: House

HOUSE in CT’s Quiet Corner: Renovated house bathed in light, with nice stunning hilltop views. Relax on its patios and small swimming pool, stroll along its forest paths, Located in New England's "Last Green Valley National Heritage Corridor" offers multiple attractions, home to many schools, universities, fairs, artists/artisans, farms, special events and year-round activities. NOTE: RENTED DOWNSTAIRS APARTMENT. OWN PRIVATE ENTRANCE. DOES NOT SHARE OUTDOOR SPACE, PATIO, OR POOL

4.92 out of 5 average rating, 278 reviews