Holiday rentals in Sutton

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Top-rated holiday rentals in Sutton

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top guest favourite

Three Adirondack chairs are positioned on the grass facing a serene lake, reflecting a beautiful sunset. The sky displays warm hues as the sun sets, casting a tranquil ambiance on the water's surface.

Cottage in Douglas

4.81 out of 5 average rating, 43 reviews

The Guesthouse at Wallis Cove

This cozy cabin features a beautiful sandy beach nestled in a private cove. Enjoy outdoor amenities including a gas grill, picnic tables, a fire pit surrounded by Adirondack chairs, and access to canoes and kayaks for water adventures. Inside, the cabin is thoughtfully equipped with modern conveniences such as Wi-Fi, Smart TV, and provided linens and towels. With space to comfortably sleep up to six guests, it’s the perfect retreat for families or small groups looking to unwind and enjoy nature.

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Top guest favourite

A colonial-style house is set among lush greenery, featuring a spacious front porch with wooden rocking chairs. Flowerbeds with potted plants line the entrance. A flag is displayed, adding character to the exterior. A gravel driveway leads up to the inviting facade.

Home in Uxbridge

5.0 out of 5 average rating, 117 reviews

Beautiful & Historic New England Colonial c.1780

The Zadock Taft House is the quintessential historic New England post & beam colonial home & listed on the National Registry of Historic Places. The house is fully climate controlled and includes 3 bedrooms, a cozy “family parlor” providing a perfect to relax and watch tv, and our wonderfully restored “tea room” and “flower room!” We invite guests to step back in time while enjoying modern day amenities! Gillette Stadium-30min. Boston-50min. Providence-25min. Newport-60min. Worcester-25min.

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Top guest favourite

Cottage in Mendon

4.95 out of 5 average rating, 155 reviews

Cozy Lake Cottage: Hot Tub, Gym & Waterfront Views

Welcome to our charming 3-bedroom lake cottage in Mendon, MA, where every sunrise paints the sky with breathtaking hues over tranquil waters. Accommodates 6 guests, making it ideal for families or couples seeking serenity. Enjoy lakeside coffee, fishing, kayaking, and evenings by the fire pit. We are pet-friendly, so feel free to bring your dogs along — if you have more than 1 dog, please let us know. Conveniently located near restaurants and attractions. Book now for a magical getaway!

ValueFamilyShared spaces

Top guest favourite

A spacious living area showcases large windows that invite natural light and views of the surrounding landscape. Comfortable seating includes a couch and armchair, complemented by a decorative fish tank. A dining table is visible in the background, enhancing the open and airy atmosphere.

Guest suite in Uxbridge

5.0 out of 5 average rating, 343 reviews

Zen Inspired Retreat with Private Forest Trails

Zig-Zag Trails blends modern comfort with the charm of rural living. Set on 65+ acres of private meadows and forests, our master guest suite is the perfect retreat to relax and recharge. Explore scenic zig-zagging trails, perfect for hiking, mountain and E-biking, and unwinding in nature—a haven for outdoor enthusiasts and homebodies alike. 📍 1 hour from Boston 📍 35 minutes from Providence 📍 25 minutes from Worcester Escape to Zig-Zag Trails—where tranquility meets adventure.

LocationFamilyWalkability

Top guest favourite

A spacious living area highlights a comfortable gray sofa, complemented by a wooden coffee table at the center. A large television is mounted on the wall, and natural light enters through multiple windows adorned with white trim.

Flat in Worcester

4.96 out of 5 average rating, 114 reviews

Centrally Located Apartment in Worcester

This first-floor unit in a charming 1910 duplex offers modern comfort and unbeatable convenience. Located within half a mile of Worcester State University and a grocery store, and within walking distance of restaurants and shops, it’s perfect for any lifestyle. The updated space features lightning-fast 1 Gbps WiFi, two workspaces, off-street parking for one car, and plenty of on-street parking. Ideal for both work and relaxation, this home is fully equipped for a comfortable stay.

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Top guest favourite

A spacious living area is presented with a comfortable sectional sofa and a coffee table. A brick fireplace serves as a central feature, while a wall-mounted television is visible. Light streams in through nearby windows, enhancing the warm ambiance of the room.

Home in Worcester

4.93 out of 5 average rating, 121 reviews

Luxury Haven: Cozy Palace

Spacious and newly renovated private house in a central but unique location next to College of the Holy Cross, very close to many restaurants, shopping mall/plaza, DCU center, Clark University, WPI and UMassMed. This newly renovated and private house is decorated to offer the comfort of home away from home with newly furnished kitchen, bedrooms, dinning, living room and office/gym space. The whole group will enjoy easy access to everything from this centrally located place.

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Top guest favourite

A single-story farmhouse features a covered front porch adorned with hanging plants. A well-maintained lawn surrounds the home, complemented by landscaped bushes. An American flag is displayed, and tall trees line the background, providing a natural setting.

Guest suite in Thompson

4.98 out of 5 average rating, 198 reviews

Meadowside: Perfect Location w/ Endless Recreation

Perfect location, great value, & tons of privacy! Come stay at Meadowside! You'll be in a beautifully appointed and completely private 620 sq ft in-law suite. We're a quarter mile away from Webster Lake and an easy drive to all area attractions! Bring your boat, as we have plenty of room for your trailer in our parking lot-sized driveway! A king bed in the master, 1.5 baths, kitchen, laundry, front farmer's porch, and garden dining! You name it, it's here at Meadowside!

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Guest favourite

Home in Woodstock

4.97 out of 5 average rating, 33 reviews

The McClellan Mansion

Resting on a sprawling estate in picturesque Woodstock, CT, this fully restored historic home blends timeless architecture with modern luxury, it offers grand spaces, cozy corners, a chef’s kitchen, spa baths, and manicured grounds. Pair with our poolside cottage for extra space and pool access. This Woodstock estate is more than a stay—it’s a destination. Pool is only included by booking the additional listing “Poolside Cottage”.

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Superhost

Flat in Sutton

4.8 out of 5 average rating, 15 reviews

Lake House w/ Private Beach, Bonfires & Fishing

Welcome to Beach & Bonfire Cove 🌊🔥 Relax at this charming Lake Manchaug retreat with a private beach, fishing, paddleboards, lakeside fire pit, and screened gazebo. Perfect for lake days and cozy nights by the water. Shared spaces include the beach, gazebo, laundry, and entrance with the upstairs occupied unit. Optional grocery pickup & stocking service available before arrival. Close to hiking, restaurants, ice cream, and more!

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Guest favourite

An open kitchen area is depicted, featuring modern appliances including a stainless steel refrigerator and stove. A dining table is positioned beside a bright window, and a washer and dryer are visible along the wall, enhancing the functionality of the space.

Flat in Northbridge

4.9 out of 5 average rating, 31 reviews

Attractive Lower Level Guest Suite

Basement Level Guest Suite with Private Entrance. 2 bedrooms, both include a queen size bed and the main living area includes 2 futons to sleep up to 6 people. Newly renovated Kitchen and Bathroom done in 2024 Open floor plan. Washer and Dryer fully functional. Off-street parking for 1 vehicle and on-street parking available for up to 2 more vehicles. Book your next stay with us at our lovely, newly renovated location.

LocationValueCleanliness

Guest favourite

A close-up of a wooden patio table is shown, featuring a central hole for an umbrella. In the background, the tranquil lake reflects the overcast sky, flanked by trees and developed areas along the shore.

Home in Webster

4.93 out of 5 average rating, 40 reviews

Webster Lake - One Home / Two Apartments

Imagine the possibilities! Perfect for large families, multiple groups, or those simply craving extra space and privacy, this unique home offers the best of both worlds: two separate, fully equipped apartments under one roof! Whether you're planning a multi-generational getaway, a reunion with friends, or need separate quarters for your group, this property provides unparalleled flexibility.

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Top guest favourite

Home in Shrewsbury

4.98 out of 5 average rating, 47 reviews

Historical New England retreat

Relax and recharge at this beautiful antique colonial home. Built in 1749 and steeped in local history, this home offers the perfect blend of classic architectural details and modern comforts. Wake to fresh eggs from our chickens, pick seasonal fruit from espaliered trees, and unwind in thoughtfully designed spaces that feel like home.

LocationFamilyLong stay