Mansion holiday rentals in Connecticut

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Top-rated mansion rentals in Connecticut

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

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Top guest favourite
A rustic barn-style home features a wooden exterior with multiple large windows, enhancing natural light. A spacious elevated deck is surrounded by lush greenery, while an outdoor umbrella offers shade. The setting is serene, with a glimpse of the nearby brook and wooded area.
Home in Fairfield
4.96 out of 5 average rating, 340 reviews

Luxurious Barn With New England Charm

Three decades of tasteful renovations — many using re-purposed material — have rendered this converted barn magazine-worthy. Set-back from the road on 1-acre of wooded land with a babbling brook, this conveniently-located modern home maintains its rustic allure. With 30-foot ceilings, exposed wooden beams, dozens of windows, an array of eclectic furniture, and a grand piano, the charm of the barn is immediately obvious. Perfect for romantic getaways, small retreats, family gatherings, and more.

Guest favourite
A serene infinity pool is framed by a natural stone deck, with views of lush greenery in the background. Sun loungers and an umbrella are positioned nearby, inviting relaxation. The pool's still water reflects the sky above, creating a peaceful outdoor space.
Villa in Morris
4.9 out of 5 average rating, 149 reviews

LuxeCompound-HotTub Pool Sauna Treehouse Gamebarn

Serene, elegantly appointed 19th century compound, fully modernized and set on the edge of a 50 acre land preserve next to boat friendly Bantam Lake. Located in the rolling hills of Litchfield County this expansive home has four buildings and every amenity: pool, hot tub, heated gym, cedar sauna, central AC, 2 chef’s kitchens, game barn, primary suite with wb fireplace and soaking tub, a pool house guest suite with steam shower, & treehouse w/ slides & a swing set built on a 300yr old oak tree.

Top guest favourite
Home in North Haven
5 out of 5 average rating, 164 reviews

Luxury Stay in Expansive Historical Home

The Bassett House, originally built in 1802, this large historic farmhouse was elegantly remolded in 2018. North Haven, CT is centrally located and just minutes from Yale, Quinnipiac, UNH, and SCSU as well as shopping, the best restaurants, hiking trails state parks and beaches, and many local attractions including various vineyards. If you’re planning a business trip or a gathering for family or friends, then our home can provide you with an exceptional level of comfort during your time in CT!

Top guest favourite
The exterior of a red two-story home is depicted, surrounded by greenery and trees. A spacious patio with large windows provides an inviting entrance. A manicured lawn stretches in front, leading to open fields and a white fence in the background under a clear blue sky.
Home in Woodbury
4.99 out of 5 average rating, 138 reviews

Your Perfectly Wonderful Woodbury Sanctuary!

Just 90 minutes from NYC, this Getaway is Perfect! Antiques, photographs, & sculptures fill this rambling, light-filled 2 story 4 bedroom 2.5 bath historic district home on Connecticut's Antique Trail. All 2,800 sq. ft of my home is at your disposal and 2 minutes from popular restaurants and diners. Your Host lives in the attached Artist Studio with its own access and parking. Stay here and you may agree with Reader’s Digest magazine that "Woodbury is Connecticut's Most Charming Small Town."

Top guest favourite
Home in Plymouth
4.99 out of 5 average rating, 100 reviews

Cozy New England Escape with relaxing hot tub

Relax and make some memories with your family and/or friends at this peaceful and cozy place to stay. This four bedroom house is spacious and unique. It has everything you need to make your stay comfortable and fun for all! We are located in a quiet wooded area with a spacious yard in close proximity to restaurants, grocery stores, and most amenities. Whether you’re relaxing on the patio, soaking in the jacuzzi or rolling around the concrete backyard skatepark it will be a memorable stay!

Top guest favourite
A cozy living area is highlighted by a soft beige sofa adorned with decorative pillows. A large area rug covers the hardwood floor, complemented by comfortable chairs. The staircase with unique short steps is visible, along with a television displaying a serene landscape.
Home in Mystic
4.99 out of 5 average rating, 190 reviews

Mystic Pearl, Charming 4 Bedroom, Downtown Mystic

DOWNTOWN LOCATION! Located just a few blocks from the Mystic river & drawbridge, this charming home is nestled in one of New England's popular waterside destinations. Enjoy short walking distance to the train station (Amtrak), downtown shops, and many awesome restaurants and bars - leave your car behind! Enjoy paddle boarding, kayaking, sailing and boating. Just down the road from the Mystic Seaport, Olde Mistick Village and the Mystic Aquarium. Includes private parking for two cars.

Superhost
An updated kitchen features a central island with three stools, complemented by light pendant fixtures. White cabinetry and stainless steel appliances create a clean, modern aesthetic. Natural light fills the space through the nearby door and large window, enhancing the inviting atmosphere.
Home in Bridgeport
4.93 out of 5 average rating, 138 reviews

Families|Charming |King Bed| Near SHU

Welcome to our updated and inviting nautical-themed residence. The home is located close to the University of Bridgeport, Sacred Hearth University and St Vincents Hospital. Enjoy the excitement of the ambiance around the fire pit in the private backyard and a grill for cooking, and the convenience of all of the amenities in the home. Guests can truly relax and make the most of their time in our tranquil setting. There is a dedicated workspace for remote workers and is family friendly.

Top guest favourite
A spacious coastal home is framed by lush greenery and seasonal foliage. The welcoming entrance features a stone pathway leading to the front door, flanked by vibrant shrubs and well-maintained landscaping. Large windows provide abundant natural light, enhancing the inviting exterior.
Home in Mystic
4.99 out of 5 average rating, 102 reviews

Lux Retreat Downtown, Near Seaport, Ping Pong

Welcome to your spacious coastal retreat in Mystic, CT—a newly furnished 5,000+ sqft haven, the largest listing in town! Set on 1.3 acres with stunning views and privacy, it’s ideal for families or groups seeking peace. Just 5 mins’ drive or 20 mins’ walk to downtown Mystic’s festive shops and dining, and 20 mins to Foxwoods/Mohegan casinos, it blends serenity with access. Perfect for fall and winter 2025 with crisp air and cozy living, hosted by dedicated Superhosts!

Guest favourite
Home in Milford
4.95 out of 5 average rating, 127 reviews

Oceanfront Beach House w/ Private Hot Tub

Escape to this luxurious 4-bedroom, 2.5-bath oceanfront home on the stunning Long Island Sound. Enjoy direct beach access, a private hot tub, and a fully equipped patio with a gas grill and dining area. Perfect for families or groups, this retreat offers breathtaking views, a full kitchen, arcade games, and modern amenities. Located minutes from restaurants and shops, it’s ideal for relaxation or adventure. Book now for a perfect blend of comfort and coastal charm.

Superhost
A welcoming entryway features a cheerful red front door and a staircase leading to the upper level. Comfortable seating in red and gray tones invites guests to relax. Decorative elements include a small side table with a clock and an arrangement of flowers.
Home in Manchester
4.81 out of 5 average rating, 145 reviews

4 BDR Cape | 15 mins to Hartford | 25 mins to BDL

I cannot wait to host you at this beautiful Cape! You will be welcomed with modern vibes and coziness. Kitchen is fully equipped. All 4 bedrooms have queen beds and black out curtains. Full bathroom comes with shower/soaking tub combo and superb water pressure. House is equipped with a office desk, chair and reliable WiFi making it suitable for a home office. The smart TV in the living room is perfect for a movie night.

Top guest favourite
The indoor heated pool features a bright blue expanse of water inviting for a refreshing swim. Comfortable lounge seating is positioned nearby, and a bar area provides space for poolside refreshments. Large sliding glass doors bring in natural light and offer views of the serene outdoor setting.
Home in Stonington
4.98 out of 5 average rating, 126 reviews

FREE Private Indoor Heated Pool - Mystic Home

Experience Mystic in style at this spacious retreat with a private year-round heated indoor pool. Sleeps up to 11 with 4 king beds + bunk, 3 full baths, and open living spaces perfect for groups. Relax poolside, cook in the gourmet kitchen, or gather on the patio by evening. Walk to downtown Mystic’s shops, restaurants, and attractions. Designed for comfort and convenience, this home is your perfect coastal escape!

Top guest favourite
An elegant two-story home features a welcoming entrance with a symmetrical layout. Lush greenery surrounds the stone steps leading to the front door. Large windows allow for ample natural light, while the architectural details add character to the facade.
Villa in New Haven
4.99 out of 5 average rating, 160 reviews

Spacious 5BR Near Yale | Ideal for Groups & Family

Welcome to Dove Haven — a peaceful and stylish retreat in the heart of Westville. Relax in the private hot tub, enjoy cozy sun-filled spaces, and walk to charming cafés, top restaurants, and beautiful Edgewood Park. Just minutes from Yale and downtown, this spacious home offers warmth, comfort, and good vibes — perfect for families, groups, and work trips seeking a relaxing escape.

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