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 Woodstock

4.94 out of 5 average rating, 231 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.

Superhost

Home in Winchendon

4.92 out of 5 average rating, 13 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 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!

Superhost

Villa in Charlton

4.77 out of 5 average rating, 66 reviews

Fall Villa near TreeHouse Brewery with King Beds

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.

Superhost

Rental unit in Fitchburg

5 out of 5 average rating, 14 reviews

Relaxing Cozy Getaway

Welcome to our charming 1-bed, 1-bath side-by-side unit, a perfect paradise with poolside access available during the warmer months! 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, whether indoors or relaxing in the backyard setup. We look forward to hosting you!

Guest favorite

Home in Brimfield

4.87 out of 5 average rating, 71 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.

Guest favorite

Guest suite in Hubbardston

4.99 out of 5 average rating, 77 reviews

Private Entry, Full Kitchen, Close to Mt Wachuset

Your home away from home is a spacious & newly renovated basement apartment /in-law suite (approx 1100 square feet), located below the main house & in walkable neighborhood. The unit has its own private entrance (bathroom, full kitchen, living room & bedroom with queen bed & extra tv). Hubbardston is a quaint little town with no stop-lights yet conveniently located to many beautiful hiking trails, fishing spots, lakes & only 15 minutes from Mt Wachusetts & 10 minutes from Rt 2 west.

Guest favorite

Farm stay in Hopkinton

4.97 out of 5 average rating, 106 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.

Guest favorite

Home in Hopkinton

4.94 out of 5 average rating, 145 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.

Guest favorite

Rental unit in Groton

5 out of 5 average rating, 71 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

Home in Worcester

4.96 out of 5 average rating, 97 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 ☞ Patio w/ zen fire table* ☞ Natural gas + charcoal grill ☞ Reverse osmosis water filter ☞ 66” smart TV projector ☞ Air filter + purifier: whole house ☞ Apple Home pod mini's ☞ Indoor gas fireplace ☞ 115 Mbps wifi For non-smokers. No smoking inside or outside. 8 mins → DT Worcester (cafe, shops, dining) 17 mins → Worcester Regional Airport ✈

Guest favorite

Guesthouse in Worcester

4.87 out of 5 average rating, 15 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 "tiny" 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. Upstairs bath with standing shower. Full kitchen and coffee and tea. Please find link to video tour under “house rules”

Guest favorite

Home in Rindge

4.91 out of 5 average rating, 23 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 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 500 ft of beautiful shoreline.