Holiday rentals in Stafford

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Top-rated holiday rentals in Stafford

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Top guest favourite
Two Adirondack chairs are positioned near a fire pit, surrounded by decorative stones and tree stumps. A view of the sparkling water and nearby houses can be seen in the background, framed by lush green trees that enhance the peaceful outdoor setting.
Cottage in Holland
4.98 out of 5 average rating, 54 reviews

Blissfully Peaceful Cottage nestled on lake

Relaxing and quaint cottage nestled on the pristine and bountiful waters of the Hamilton Reservoir. Perfect place to step back with the family and take a much needed timeout to reconnect with your loved one(s). The reservoir is pristine and is clear up to 4’ down. Perfect for swimming or just relaxing on the private beech located steps away. Be our guest, come out and enjoy this peaceful place and take the time to make memories that will last a lifetime. Looking forward to hosting you!

Guest favourite
Home in Stafford
4.94 out of 5 average rating, 100 reviews

Serene Lakefront Retreat

This idyllic 2-bedroom, 2-bath lakefront retreat on scenic Staffordville Lake accommodates up to 6 guests (4 beds), offering an unforgettable experience for your family. Enjoy breathtaking views from the cozy living area or the private deck. Kayak (2 included), swim off the floating dock, stargaze, grill out and enjoy your coffee on the deck! Separate workspace and free Wi-Fi for those working from home. Perfect for Brimfield Antique attendees. Book now for a relaxing getaway!

Top guest favourite
A comfortable studio space is highlighted by a plush queen bed adorned with white bedding, positioned beside a cozy fireplace. Soft light is provided by a bedside lamp, while a fan offers air circulation. Neutral tones and warm accents create a welcoming ambiance.
Flat in Wilbraham
4.99 out of 5 average rating, 153 reviews

Western Mass Retreat!

Western Mass Retreat! Come relax and unwind in this updated retreat and check out all the amazing things that Western Mass and Northern CT have to offer. Enjoy the cozy reading nook, outdoor space, or a relaxing dinner in at the dinette table. Centrally located near multiple colleges and universities, two miles from Wilbraham & Monson Academy, ten minutes from GreatHorse and close to many one-of-a-kind events and experiences. Please message me with any questions.

Top guest favourite
The stone barn building is framed by vibrant lavender fields in the foreground. Evening light illuminates the windows, while a calm sunset creates a soft gradient in the sky, transitioning from warm hues to deep blues.
Barn in Holden
4.9 out of 5 average rating, 532 reviews

Farm stay in a Historic Ski Lodge turned Barn

Once a ski lodge, then a horse barn, the hayloft in this unique stone barn has been converted to a comfortable & peaceful getaway. Enjoy a tranquil farm stay on a working Lavender farm. Help feed (if you wish) the horses and ponies and see the chickens. Enjoy the serene views and take in a sunrise or sunset or the stunning evening stars and moon on the back patio, stroll around the farm and hike our 1 mile nature walk. Convenient to local skiing & golfing.

Top guest favourite
A charming two-story house is framed by lush green trees and manicured lawns. The front porch offers an inviting entrance, while large windows allow for natural light. The surroundings are peaceful, enhancing the serene country setting.
Flat in Ashford
4.96 out of 5 average rating, 213 reviews

On The Run Farm

Quiet country setting, minutes from UCONN and easy access from RTE 84 makes this place perfect for visitors traveling through the "Quiet Corner" of CT. Spacious living room, bedroom. kitchen and bath are newly renovated with, hardwood floors, skylights, and windows that allow for lots of natural light. The entryway is private with a lovely porch that is a great place to sit with your morning coffee. Hiking trails can be accessed from the property.

Top guest favourite
A serene riverside deck features two striped lounge chairs, positioned for optimal views of the Connecticut River. Lush greenery frames the scene, and flower pots add a touch of elegance. The wooden deck offers a natural and inviting space to relax by the water.
Home in Agawam
4.97 out of 5 average rating, 243 reviews

Sunrise on the Water's Edge - Riverside Bungalow

Cozy riverside bungalow celebrates panorama views of the peaceful Connecticut River. Multiple levels of outdoor living space, open-air and screened-in. Just minutes from all major points of interest in the Pioneer Valley - including Six Flags New England, MGM Casino Complex, Big E Fairgrounds, Basketball Hall of Fame, and the Greater Springfield Metro area. Only 20 minutes from Bradley International Airport (BDL) in Windsor Locks.

Top guest favourite
The treehouse is elevated on wooden stilts, surrounded by vibrant autumn foliage. Large windows reflect warm light, showcasing a rustic wooden exterior. A staircase leads up to the entrance, inviting guests to explore this serene retreat among the trees.
Treehouse in Willington
4.92 out of 5 average rating, 529 reviews

Treehouse - Countryside - Farm Animals - Fire Pit

Escape to the stars in the Private Treehouse nestled among the trees at Bluebird Farm Connecticut. Amenities: ● 100+ Mbps Wi-Fi | Outdoor Fire Pit | Indoor Fireplace ● Interaction w/ Farm Animals | Year-Long Running Water (Sink/Shower) ● Kitchenette | AC in Unit | Free Coffee | Board Games | Books Drive To UCONN (10 Mins) | Hartford (30 Mins) | Boston (1 Hour) | NYC (2.5 Hours)

Guest favourite
Tiny home in East Lyme
4.99 out of 5 average rating, 153 reviews

Waterfront Bliss Tiny Home

Lakeside Bliss in a Tiny Package Step into a world of relaxation at this cozy tiny house on Pattagansett Lake. In addition to the huge picture window overlooking the beautiful natural lake setting, the tiny house is equipped with a queen bed, full kitchen, high speed Wi-Fi, and unmatched ambiance. Perfect for nature lovers or couples looking for a unique stay by the lake!

Guest favourite
An open living space features a cozy sleeping area with a spacious bed and decorative bedding. A television is positioned on a wooden stand facing the bed. Exposed brick walls and industrial lighting create a warm ambiance. A lofted shelf with greenery adds a touch of nature.
Flat in Stafford
4.95 out of 5 average rating, 175 reviews

Modern Industrial Apartment with rooftop access

* Modern industrial apartment with rooftop access. * Nestled in an old Mill Building/Artist Community. * Centrally located between Boston and NYC. * 15 mins to UConn, 20 mins to Brimfield Antique Show. * 40 mins to MGM Casino in Springfield, MA. * Walk to restaurants, boutiques, parks, and events. * On-site Yoga, Dance, Recording Studio & Vintage Shop.

Superhost
Flat in Stafford
4.84 out of 5 average rating, 173 reviews

Historic Two Bedroom

Cozy 2BR first-floor apartment in a historic 220-year-old building in Stafford, CT. Fully renovated interior with modern comforts, full kitchen, fast Wi-Fi, and self check-in. Sleeps up to 4. Walk to downtown shops and dining, near UConn. Street parking plus limited private parking. Note: exterior is still being updated. No pets.

Top guest favourite
The kitchen features dark wood cabinetry and a spacious island with bar seating for two. A small dining setup is placed on the island, complemented by decorative plants on the countertop. Natural light fills the room through a large window, creating a bright space.
Flat in Ellington
4.98 out of 5 average rating, 110 reviews

Cozy Apartment in Ellington

Cozy 2nd floor apartment in residential area, located between Hartford and UCONN. Close access to interstate 84 and 91. A small town feeling with access to local good eats and shopping. For those nature lovers we are located close to Shenipsit Lake with walking, hiking and fishing. Numerous parks, playgrounds and trails nearby.

Top guest favourite
Guest house in Stafford
4.96 out of 5 average rating, 109 reviews

A Barn Experience $159/night NO cleaning fee

A unique, spacious and serene space w plenty of parking…views of backyard pond and field. Walking trails through over 10 acres of forest. So private yet less than 3 miles to Stafford Motor Speedway and downtown Stafford Springs.

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