Vacation rentals in Prospect

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Top-rated vacation rentals in Prospect

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Guest favorite
A serene bedroom includes a spacious bed dressed in neutral linens, accented with a textured throw and decorative pillows. Natural light filters in through a window, and a soft area rug complements the decor. A modern chair and bedside tables enhance the inviting space.
Apartment in Meriden
4.91 out of 5 average rating, 35 reviews

Hillside Retreat

Welcome to our little hillside hollow, tucked away on the east side of Meriden. I am a gardener and enjoy cultivating a wildlife habitat on our property. The retreat has been carefully designed for tranquility. It features a galley kitchen with a reading nook, a tiled bathroom, and a sweet bedroom with a small private deck overlooking the back yard, trees, and walking path. While the retreat feels rural, it is convenient to downtown, and to the noted hiking trails in the center of the state.

Top guest favorite
A brick fireplace is centered against a light green wall, featuring a clock above it. A patterned chair is positioned nearby, alongside a small television stand. A woven rug covers the floor, enhancing the cozy atmosphere of the space.
Guest suite in Watertown
4.91 out of 5 average rating, 209 reviews

Lrg Studio Apartment - walk to Taft

Welcome to my downstairs space! This clean open concept space is ready for your long term or overnight stay. This studio space is the lower level of a raised ranch house. I live upstairs with my dog and share laundry with airbnb guests. The space has a private entrance through the garage, private bath, and kitchen area in a quiet neighborhood. Walking distance to Taft and convenient to Rts 8 & 84. Off street pkg. Whether you are interested in two nights or two months, you are welcome here!

Top guest favorite
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
4.94 out of 5 average rating, 175 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 favorite
A panoramic view showcases vibrant autumn foliage across rolling hills, with colors ranging from deep reds to bright yellows. The scene is framed by lush greenery in the foreground, while rooftops and distant landscapes are visible in the background under a clear blue sky.
Home in Waterbury
4.95 out of 5 average rating, 126 reviews

Amazing views of the Brass City

East Mountain Views at its finest. This clean, 3-bedroom newly 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 (month of July). Wi-Fi/cable, central AC/hot air, washer/dryer, and grill are included with the stay. Plenty of entertainment (board games, corn hole, foosball, air hockey table) are provided. This house is truly relaxing and will feel like home.

Top guest favorite
A tranquil outdoor scene features a lush green lawn surrounding a calm pond. The reflection of trees and the nearby home can be seen in the water. A picnic table sits on the grass, inviting relaxation amidst the natural surroundings.
Home in Southington
4.94 out of 5 average rating, 123 reviews

Connecticut Chalet: Experience Fall in New England

Escape to a unique & stylish home perfectly tucked away in a picturesque New England town. Indulge in the privacy & serenity of this 5 acre wooded property and peaceful pond while being minutes from an abundance of restaurants, shops & entertainment. Enjoy the natural setting from the comfort of the glass enclosed sunroom with panoramic views of the property. This 3 bed, 2 bath home maintains it’s original 1960’s charm while boasting thoughtful modern touches and intentional functionality.

Top guest favorite
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, 135 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 favorite
Home in Wolcott
5 out of 5 average rating, 12 reviews

Wake Up on the Water, Ski by Noon

Enjoy lakefront living at its finest on Lake Hitchcock! This 3 bed, 2.5 bath sleeps 6 with an open plan, entertainer’s kitchen, and lake-view porch. Step to your private dock for kayaking, fishing, swimming, and sunrise/sunset magic. Cap the night at the fire pit. Winter? You’re about 10 minutes to Mt. Southington. Year-round, Downtown New Haven and Hartford are an easy drive for dining, museums, and nightlife. The ultimate escape—book now and make memories by the lake!

Top guest favorite
A serene lakeside view features a well-maintained lawn leading to calm waters. Two comfortable yellow chairs are positioned on the grass, offering a perfect spot for relaxation. Trees frame the setting, while distant homes can be seen along the shoreline, enhancing the peaceful ambiance.
Home in Wolcott
4.81 out of 5 average rating, 16 reviews

Cozy Waterfront Lake House

Relax at this peaceful 1BR lakefront retreat—perfect for couples or small families. Summer: Enjoy kayaking, swimming, grilling, outdoor dining, and fire pit s’mores. Off-season stays offer crisp hikes, lake views, fires, nearby skiing at Mt. Southington (5 mins), and family fun at Lake Compounce. Sleeping arrangements include a queen size bed in a Bedroom, a pullout sofa bed and a queen sized blow up mattress. Self check-in, fresh linens, and a welcoming vibe await.

Top guest favorite
A spacious living area features a plush sectional sofa adorned with decorative pillows. A rectangular coffee table sits in the center, accompanied by a small potted plant. Natural light enters through a window, while a private entrance door is visible in the background.
Guesthouse in Southington
4.95 out of 5 average rating, 22 reviews

Cozy Private Guest Suite

Welcome to your perfect home-away-from-home in Southington, CT! This private basement guest suite offers a cozy, quiet escape with everything you need for a comfortable stay. Whether you're visiting for business, or just passing through, you'll enjoy a peaceful space with a private entrance, living area, and essential amenities. Free parking on premises Located in a quiet neighborhood just minutes from local restaurants, walking trails, and easy access to I-84

Top guest favorite
The exterior of the two-story home is showcased, featuring a light-colored facade with multiple gabled roofs. A well-maintained lawn surrounds the house, accented by blooming shrubs. A paved driveway leads to a two-car garage, and trees provide a natural backdrop.
Apartment in Waterbury
4.99 out of 5 average rating, 107 reviews

Everything you need! Apartment!

Awesome bright 2nd floor apartment, has everything you need for your stay. Full Kitchen, Laundry and is in an very convenient and safe area. Walking distance to several restaurants and bars. Easy access to highway. Parking is available behind left garage, which may be available. Ask for details. Quiet area, On cul-de-sac. Wi-Fi, Netflix, Prime,Hulu FYI: I host a friendly card game every two weeks in the garage till 11:30 PM.

Top guest favorite
A round wooden table is set with woven placemats, featuring a white cup filled with frothy coffee. A tall vase with a vibrant sunflower adds a touch of color, while a small tray with assorted snacks is visible in the background.
Apartment in New Britain
4.96 out of 5 average rating, 223 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 favorite
An elegant Arts & Crafts bungalow showcases a blend of architectural styles under a clear blue sky. The inviting façade features a distinctive porch, a brick chimney, and a nearby garage. Lush gardens adorned with vibrant plants enhance the home’s outdoor appeal.
Guest suite in Wallingford
5 out of 5 average rating, 621 reviews

Wintergreen Gardens Suite @ William Becroft House

LGBTQ friendly. Our 1915 Arts & Crafts bungalow's spacious in-law suite offers driveway parking, private entrance, sunroom, king bedroom, en-suite bath, kitchenette w/fridge, micro, coffee maker, toaster. Relax in bed with 40" HDTV with Amazon Prime, HBO Max, Netflix, premium cable. Enjoy private gardens to sun, read a book or cup of coffee. Short drive to 4 Vineyards, Theater and the train station.

Popular amenities for Prospect vacation rentals