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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Villa in Charlton

4.75 out of 5 average rating, 55 reviews

Summer Villa: Private Pool, Playground, 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.

Nov 13 – 20

$370 per night

Superhost

Home in Winchendon

New place to stay

Amazing Lakefront Home with Pool- Tatum's Place

Bring the whole family to this great place with lots of room for fun. Escape to our stunning waterfront property on Lake Monomonac! With 200 ft of lake frontage, private boat docks, it's the perfect year-round getaway. Enjoy spacious living with 5 bedrooms, 4 baths, and TWO kitchen. Summer fun includes boating, swimming. In the winter, snowmobiling + skiing . Close to many amenities makes it ideal for families. Book now and experience unforgettable memories at our paradise by the lake!

Oct 27 – Nov 3

$609 per night

Guest favorite

Farm stay in Hopkinton

4.97 out of 5 average rating, 95 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.

May 31 – Jun 7

$317 per night

Guest favorite

Home in Woodstock

4.93 out of 5 average rating, 207 reviews

Cedar Ridge

In Connecticut's "Quiet Corner", a fully renovated 2-level house bathed in sunlight, with lovely 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.

Oct 23 – 30

$243 per night

Guest favorite

Apartment in Groton

5.0 out of 5 average rating, 50 reviews

Farmhouse Guest Apartment

Welcome to our quiet private guest apartment! Our property, is surrounded by fields, woods, walking trails, 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.

Apr 16 – 23

$141 per night

Guest favorite

Home in Hopkinton

4.95 out of 5 average rating, 138 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.

Jul 17 – 24

$136 per night

Guest favorite

Guest suite in Hubbardston

5.0 out of 5 average rating, 25 reviews

Private Entry, Full Kitchen, Close to Mt Wachuset

Your home away from home is a spacious and newly renovated basement apartment /in-law suite (approx 1100 square feet) in a quiet walkable neighborhood with its own private entrance (bathroom, complete kitchen, living room and bedroom with a queen bed and extra tv). Hubbardston is a quaint little town with no stop-lights yet conveniently located to many beautiful hiking trails, fishing locations, lakes and only 15 minutes from Mt Wachusetts and 10 minutes from Route 2.

Sep 10 – 17

$85 per night

Guest favorite

Home in Worcester

4.95 out of 5 average rating, 83 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 ✈

Jul 11 – 18

$246 per night

Guest favorite

Place to stay in Northborough

4.94 out of 5 average rating, 63 reviews

Peaceful 2 Bedroom Getaway Next to Mid-Century Gem

Nestled in the woods on the grounds of a historic mid-century gem, enjoy the elegant and secluded setting surrounded by nature with a rolling meadow, towering trees and a variety of evergreens. Wake up to the sound of birds and cozy up in front of the wood burning stove with a hot cup of coffee. This charming two-bedroom cottage with vaulted, beamed ceiling, field stone fireplace & wood stove, is a true getaway from the hustle and bustle of city living.

Sep 21 – 28

$272 per night

Cabin in Brimfield

Cozy Campground Cabin 2 by lake

Ammenities include a pool, beach access, private bathrooms, a rec hall with weekend activities, and more! Our cabins come equipped with a bunk bed with full mattresses, a kitchenette with mini fridge, coffee maker, and microwave. You will have your own private bathroom with a shower, toilet and sink. Our cabins come equipped with cable and a flat screen TV for when you want to sit back and relax after a long day of enjoying the beautiful lake.

Sep 22 – 29

$73 per night

Guest favorite

Farm stay in Rutland

4.97 out of 5 average rating, 317 reviews

Farm Living

We offer a quiet country setting on a small working farm, with cows, horses, pigs, goats, 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 or replace and enjoy the peacefulness. Please inquire about kayak rentals.

Dec 26 – Jan 2

$129 per night

Guest favorite

Cabin in Hubbardston

4.94 out of 5 average rating, 140 reviews

Triggers Cabin

Cabin in the woods on a stocked trout pond. Outside deck over the pond for quietly relaxing. Outside fire pit. Gas grill. Inside fireplace.Located in a small private quiet campground. On 200 acres of private wooded land in central Massachusetts. Located on hiking trails that are also used for biking & horseback. Bring your own linens....but kitchen fully equipped. A great place to enjoy the out doors & disconnect & recharge..

Dec 4 – 11

$135 per night