Holiday rentals with a pool in Worcester County

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]✈

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.

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!

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.

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!

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!

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.

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.

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.