
Holiday rentals in Eastford
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Top-rated holiday rentals in Eastford
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Serenity Ashford Lake
Serenity Ashford Lake is truly a gem far from the hustle and bustle of everyday life, while still enjoying all the creature comforts. Situated on the shores of tranquil Ashford lake, the Serenity lake house is definitely your place to relax and unwind. Waterfront jacuzzi, gazebo, central air, stainless steel appliances, cozy linens, washer/dryer, kayaks, firepit, boutique toiletries and a new kitchen space make up this beautiful lake home. Bring your favorite books, relax, and enjoy lake time!
4.91 out of 5 average rating, 124 reviews
Mid-Century Modern Lakefront Cabin
Welcome to our 1966 Scandinavian mid-century modern cabin in the woods . Renovated with every modern amenity, and lake views out every window. With direct lake access & shallow waters, it’s great for families with young children. Perfect for wedding party prep & lakefront photos! In "The Quiet Corner" near UCONN, Eastern, Woodstock/Pomfret Academies, Clark + Trinity, wine trail, hiking, antiques & farm stands. Our place isn’t for big parties. It’s quiet & geared toward family & friends.
4.94 out of 5 average rating, 81 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!
4.94 out of 5 average rating, 110 reviews
Clark Cottage in the historic village in Chaplin
Up to 14 day stays are OK. This rustic cottage, circa 1850, has antique charm, yet modern comforts. In addition to a living and dining room, there is a vintage kitchen, 2 bedrooms, 1 bathroom, laundry facilities. Very tall people will have to duck under door ways. Not suitable for children under 12. WiFi and a smart TV. Kitchen ceiling is 6'3.5". An exterior camera is installed to observe wild life passing through the yard. A switch in the laundry turns it off.
4.89 out of 5 average rating, 157 reviews
Barn suite at Southwood Alpacas
Country living at its best. Renovated guest space on a working alpaca farm. This is a two story unit with a kitchenette, living room and bathroom on the first floor and a studio loft on the second floor. Two decks, one on each level overlook the farm. Recently renovated. Great light floods the unit. Central heat & AC. Enjoy the farm and the bucolic setting in Woodstock. Watch the alpaca from your windows or deck. Cafes for morning breakfast and fine dining await.
4.98 out of 5 average rating, 237 reviews
Secluded 2 Acre Lake Front Home!
Escape to this breathtaking retreat on Lake Chamberlain, tucked away in Connecticut's serene "Quiet Corner". This spacious 2-acre home offers total privacy and stunning natural beauty. In the summer, dive into swimming, fishing, and kayaking 🛶🏊♀️. When winter arrives, experience ice skating ⛸️ right on the lake! Whether you're here for relaxation or adventure, this peaceful getaway will steal your heart. Once you arrive, you may never want to leave! 🏡💖
4.85 out of 5 average rating, 139 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.
4.96 out of 5 average rating, 222 reviews
Affordable In-Law Apartment in Brooklyn, CT
This is a great in-law style apartment which was fully renovated in 2020. It can be booked for short stays or more lengthy visits to Northeast CT. The apartment is one minute from Scenic route 169 and Route 6. It is 30 minutes to UCONN and ECSU. We are close toThe Pomfret School/Rectory School. It is 35 mins to Mohegan Sun and Foxwoods. My place is rural and peaceful. It is good for couples, solo adventurers, business travelers, and families.
4.94 out of 5 average rating, 242 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”.
4.97 out of 5 average rating, 33 reviews
Enjoy a Farm Stay without the Work
This 3-room one-story apartment with private entrance is attached to the main 1850 farmhouse and also has that older farm charm. Only 10 minutes to Interstate 84 and midway between New York City and Boston, this location allows for ease of access to experiences in the northeast. The property is set back from the state road (Route 89) and allows for relaxed living on a beautiful farm bordered by stone walls and wooded area behind.
4.98 out of 5 average rating, 285 reviews
Spacious, unique barn with beautiful views.
Our barn is in a large field on lot next to our home. Our rental area is upstairs which offers beautiful views of our field and the visiting deer. The eclectic decor is accumulated from years of activism. Our guest room and bathroom are newly renovated. It is a quiet and peaceful area near two state parks. We operate a mail order business in the downstairs area but will not be working while guests are staying with us.
4.95 out of 5 average rating, 177 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)
4.93 out of 5 average rating, 549 reviewsPopular amenities for Eastford holiday rentals
Other great holiday rentals in Eastford

Handcrafted Timber Frame Cabin Retreat
5.0 out of 5 average rating, 39 reviews
Hillside Haven
5.0 out of 5 average rating, 33 reviews
Quiet Corner Studio
4.97 out of 5 average rating, 39 reviews
The Barn at Pondview
5.0 out of 5 average rating, 56 reviews
Wings & Wildflowers at the Glen
4.94 out of 5 average rating, 34 reviews
Woodstock Suite
4.88 out of 5 average rating, 26 reviews
Sandy Beach House
4.91 out of 5 average rating, 58 reviews
Little Rest Studio
5.0 out of 5 average rating, 82 reviewsDestinations to explore
- Gillette Stadium
- Mohegan Sun
- Foxwoods Resort Casino
- Six Flags New England
- East Matunuck State Beach
- Bonnet Shores Beach
- Ocean Beach Park
- Charlestown Beach
- Mystic Seaport Museum
- Mystic Aquarium
- Easton Beach
- Roger Williams Park Zoo
- University of Connecticut
- University of Rhode Island
- Soundview Beach
- Powder Ridge Mountain Park & Resort
- Easton's Beach
- Ocean Beach
- Dcu Center
- Ski Sundown
- Fort Adams State Park
- Clark University
- Wesleyan University
- University of Massachusetts Amherst





