Holiday rentals in Ashford

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Top-rated holiday rentals in Ashford

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Guest favourite

The charming lake house features a sun-themed front entrance, flanked by dark shutters. A welcoming path leads to the door, surrounded by lush greenery and flower beds. The serene lake can be glimpsed through the trees in the background, enhancing the tranquil setting.

Home in Eastford

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, 122 reviews

Superhost

A bright and inviting open-concept living area features two vibrant blue armchairs adorned with floral patterns. A wooden dining table is visible in the background, with a fully equipped kitchen displaying colorful cabinetry and modern appliances. Soft light enhances a welcoming atmosphere.

Home in Ashford

Lake - King - Gym - Kayak - Fire Pit - Pets Allowed - WD

4.86 out of 5 average rating, 140 reviews

Top guest favourite

Tiny home in Mansfield

Handcrafted Timber Frame Cabin Retreat

Escape to the woods and slow things down at this beautifully handcrafted timber frame cabin, tucked away among towering trees and nature’s quiet. Built with exposed beams, natural wood, and timeless craftsmanship, this cabin blends rustic charm with modern comfort—perfect for a romantic getaway, creative retreat, or unplugged weekend escape. Whether you’re looking to reconnect, recharge, or simply enjoy the beauty of the forest, this timber frame cabin offers a warm and memorable escape.

5.0 out of 5 average rating, 37 reviews

Guest favourite

Home in Stafford

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!

4.93 out of 5 average rating, 107 reviews

Guest favourite

The cottage features a charming blue exterior, framed by a manicured lawn with greenery. Windows are adorned with white shutters, and a welcoming front porch is accessible via a small set of steps. Tall trees provide a natural backdrop, enhancing the serene setting.

Cottage in Chaplin

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

Guest favourite

The exterior of a charming green house is framed by vibrant flowering shrubs and manicured lawn. A prominent brick chimney rises from the roof, surrounded by lush greenery that enhances the home's inviting presence.

Home in Woodstock

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

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

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

Top guest favourite

The bungalow is framed by lush greenery, featuring a blend of light and brick-colored siding. An American flag is displayed prominently at the front. A gravel driveway leads to the entrance, which is highlighted by a stone border and surrounded by a manicured lawn.

Home in Mansfield

3 Bed 1.5 Bath 1 mile to UConn

Consider this bungalow your home away from home while you visit Storrs. We are one mile from the UConn campus on a private 4+ acres. This lovely property features 3 bedrooms with a queen, king, and full bed, perfect for a family or group of friends. With 1 full bathroom and 1 half bath, that is attached to bedroom one. We have essential amenities like WiFi, AC, Fubo TV and a dishwasher, washer dryer upon request. Shared front entrance.

5.0 out of 5 average rating, 49 reviews

Guest favourite

A rustic cabin exterior is presented, featuring a stone chimney and wooden siding. Lush green grass surrounds the property, with a gravel driveway leading to the entrance. Trees provide shade, enhancing the tranquil outdoor setting.

Home in Ashford

Amazing lake home w/ amenities.

Escape to Lake Chaffee! This bright, airy lakefront home is peaceful and relaxing, with a private master, loft with twin bed, futon, and rollaway cot; perfect for couples or families. Paddle the lake, unwind by the fire pit, or cozy up indoors with Wi-Fi. Enjoy serene views year-round and unplug in comfort. Very quiet neighborhood on dead end street that lets you walk to one of the two beaches on the lake. You won’t be disappointed!

4.85 out of 5 average rating, 136 reviews

Guest favourite

The living room showcases a comfortable seating area with a dark couch, complemented by a glass dining table nearby. A wooden mantel above a decorative fireplace adds warmth, while natural light filters through the large windows, illuminating the soft white walls.

Flat in Ashford

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, 283 reviews

Guest favourite

A spacious barn is situated in a large field, surrounded by greenery. Its two-story structure features a combination of windows and a central door, offering access to the outdoors. Lush grass and various plant life contribute to the serene rural setting.

Guest house in Hampton

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, 176 reviews

Top guest favourite

Home in Ashford

Lakefront Retreat w/ Stunning Water Views

Lakefront cottage in the “quiet corner” of northeastern Connecticut, thoughtfully loved and well cared for. Start mornings with coffee by the water, spend days kayaking, rowing, or floating on the lake, and unwind at night by the firepit. Cozy up in the three-season lake room with a fireplace when it turns chilly. Peaceful, cozy, and conveniently near UConn—your perfect New England lake escape.

4.97 out of 5 average rating, 31 reviews