Holiday houses in Prospect

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Top-rated holiday rentals in Prospect

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

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Guest favourite
Home in Waterbury
4.96 out of 5 average rating, 139 reviews

Amazing views of the Brass City

East Mountain Views at its finest. This clean, 3-bedroom updated ranch is centrally located to highways and shopping centers. Walk out to the back deck and experience some of the best views of Waterbury including Fireworks from the back deck (July). Wi-Fi/cable, central AC/hot air, washer/dryer, and patio furniture/grill (seasonal) are included with the stay. Plenty of entertainment (board games, corn hole, foosball, air hockey) are provided. This house is truly relaxing and will feel like home.

Top Guest favourite
A studio layout features a queen-sized bed with neutral bedding, situated under a sloped ceiling with recessed lighting. A small dining table and two chairs are positioned near a closet. A Smart TV is mounted on the wall, complementing the wooden flooring.
Guest suite in Cheshire
4.95 out of 5 average rating, 208 reviews

Cozy & Private Studio Suite

Quiet and private in-law suite. Located close to the center of Cheshire, convenient to Route 10, I-691, and Route 15. Near to grocery stores, great restaurants, and shopping centers. 15 minute drive to Toyota Oakdale Theater, 20 minute drive to Lake Compounce Amusement and Water Park, and 30 minute drive to Yale University, Museums, and downtown New Haven. A slightly longer drive will take you to to the beautiful shoreline, Hammonasset Beach State Park, Foxwoods and Mohegan Sun Casinos!

Guest favourite
The entrance showcases a wooden door with a rustic design and a blue frame. A yellow flower arrangement hangs from the door, welcoming guests. The space beyond is an open-concept living area with natural light filtering through sheer curtains, revealing a sectional sofa and wood ceiling beams.
Cottage in Bethlehem
4.99 out of 5 average rating, 148 reviews

Cozy Cottage |Quintessential CT | Pet Friendly

Escape to the Cottage at the Grove - with a cozy wood burning fireplace and inviting sectional it is the perfect winter sanctuary. Well equipped with all the amenities; from a fully stocked kitchen to bath salts for the deep soaking tub. One bedroom w/ en-suite bath & pull-out full size sofa bed. Just 30 min to Mohawk or Southington Ski Mountains. Just 10 min to downtown Litchfield, close to local farms & vineyards. For security we have two exterior cameras facing the door & driveway.

Top Guest favourite
The exterior of a bright red carriage house is surrounded by lush gardens filled with various flowers and greenery. Two large windows and a white door are visible, adding charm to the traditional New England design. A well-maintained lawn complements the vibrant landscape.
Guesthouse in Wallingford
5 out of 5 average rating, 151 reviews

The Garden Loft - A Charming Choate Stay

Welcome to The Garden Loft! Located in the heart of downtown Wallingford, CT. This traditional and historic New England carriage house has been completely renovated in the summer of 2022 into a peaceful, cozy, bright & airy loft. We are a 3 minute walk from downtown where you will find a variety of restaurants, bars, a brewery & only 1 mile from from Choate Rosemary Hall. A 15 minute drive to Yale University & downtown New Haven. Get ready to relax, get cozy & enjoy The Garden Loft!

Top Guest favourite
A cottage nestled in a lush green setting is highlighted, surrounded by trees. The lawn is spacious and well-maintained, featuring a hammock between two trees. The structure showcases a simple facade with light blue siding, white window frames, and a chimney.
Home in Newtown
4.99 out of 5 average rating, 127 reviews

Comfortable home away from home- near everything

Price includes Airbnb fees. Cozy, pet-friendly cottage in a peaceful setting just 70 miles from NYC and minutes from I-84 (Exit 8 or 9). This clean & comfortable retreat features 3 bedrooms (2 queens, 1 full), and pull-out couch. Portable A/C's in summer, and fireplace for cozy nights. The greenhouse adds plenty of natural light, the yard is perfect for kids, the front deck is great for morning coffee, and the gas grill great for cooking out. High-speed WiFi and 3 smart TVs.

Top Guest favourite
A cozy living room features a spacious blue couch adorned with yellow accent pillows. A wooden coffee table is positioned in front, with colorful artwork hanging on the walls. A large flatscreen TV is mounted for entertainment, enhancing the comfort of the space.
Apartment in Westville
4.98 out of 5 average rating, 133 reviews

Retreat in New Haven by Stephanie and Damian

Welcome to your retreat in the heart of Westville. This apartment features a spa-like bathroom and a cozy living room with a super-comfy couch and large flatscreen TV. Relax in this centrally located oasis near Yale’s football stadium, Westville Bowl, local art studios, coffee shops, and top restaurants just steps away. Perfect for extended stays, traveling professionals, visiting faculty, or anyone seeking a convenient home base this winter. Discounts for stays of 30+ days.

Top Guest favourite
The spacious loft features a sloped ceiling with exposed beams, accommodating a king-size bed and a cozy sofa. A work table is positioned beside a large window that allows natural light to fill the room. A flat-screen TV is mounted on the opposite wall.
Cottage in Collinsville
4.96 out of 5 average rating, 158 reviews

The Carriage House Skiing Nearby

Newly built contemporary light filled spacious 700 ft carriage house/Loft. It is walking distance to the Farmington river and downtown historic Collinsville. Just off the cycling "rails to trails" river trail, you'll find places to also kayak, SUP, fish and swim. CT Wine Trail and Brignole Vineyards nearby where you'll find food trucks and live music along with award winning wine! Skiing nearby. Conveniently close to Farmington, Avon, Simsbury, West Hartford and 84 highway.

Top Guest favourite
A modern living space features a comfortable sofa, a circular coffee table, and a television unit. Large sliding glass doors create a seamless view of the outdoors, with natural greenery visible beyond the private deck. Soft natural light fills the room, enhancing its inviting ambiance.
Guesthouse in Guilford
4.99 out of 5 average rating, 512 reviews

Get Back to Nature at a Modern Wood Clad Getaway

HAPPY SPRING… The spring birds are arriving and the crocuses are up. Hawks, cardinals, blue jays, bluebirds, gold finches and more are here. Beautiful hiking trails in the woods and along the beachfront. Great places to shop and eat or catch a show at one of New Haven’s renowned museums or broadway theatres or relax. Great restaurants along the shore. Enjoy! We want you to have a relaxing stay with us, free from worry. We are located in a private area, away from public.

Top Guest favourite
Home in Milford
4.96 out of 5 average rating, 134 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.

Top Guest favourite
A timber-style cottage is surrounded by landscaping featuring stones and low shrubs. A spacious deck with white railings leads to a welcoming entrance. Light-colored siding and multiple windows enhance the two-story structure, set against a backdrop of trees and open land.
Home in Southbury
4.99 out of 5 average rating, 151 reviews

The Cottage at Cedar Spring Farm

Welcome to The Cottage at Cedar Spring Farm located on a 16 acre working Christmas tree farm bordered by 155 acres of protected land trust with marked hiking trails. The holidays are right around the corner. Holiday reservations have date restrictions. Please inquire about availability. Conveniently located to I-84, shopping, local farms, wineries, breweries, restaurants, and Heritage Village. Please note that we allow pets (dogs only) and have a limit of two.

Top Guest favourite
Apartment in New Britain
4.96 out of 5 average rating, 257 reviews

Spacious Cozy Guest Suite

This unique guest suite located in a newly constructed home offers over 600 sq ft of space. There is a private entrance in a quiet and safe location. Minutes from CCSU, UCONN Med Center, I-84, downtown, restaurants and shopping. West Hartford Center is only 10 minutes away. KITCHEN DOESN’T INCLUDED STOVE , fridge, microwave, fully stocked coffee bar. Smart TV, high speed internet and work space are perfect for remote work.

Top Guest favourite
A sunlit porch area features a spacious bed adorned with a white quilt and colorful accent pillows. A striped rug lies on the floor, while wicker furniture and large windows create an airy atmosphere. Natural light fills the space, offering views of the outdoors.
Cottage in Guilford
4.94 out of 5 average rating, 282 reviews

The Cottage at Indian Cove

A charming original turn of the century cottage that was recently renovated. One main room plus a full bathroom and Ikea kitchen. It includes a back porch that gets a perfect amount of late afternoon sun. The cottage has electric baseboard heat for cool nights. We are located in Indian Cove beach Association with a two block walk to the beach. You are welcome to enjoy our kayaks, bikes to tour the area and a fire pit.

Popular amenities for Prospect holiday rentals