Vacation rentals in Seymour

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Top-rated vacation rentals in Seymour

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Guest favorite

An open bedroom suite is featured, with a warm-colored comforter covering a spacious bed. A wooden dresser stands beside the bed, and a leather couch is positioned against the wall. Natural light enters through windows, brightening the neutral-toned walls.

Guest suite in Ansonia

4.74 out of 5 average rating, 511 reviews

Private Inn

Private(not shared) self check-in, clean, quiet, safe, and free off street parking on a cul de sac road. The suite is 600sq your own private bathroom, backyard, and number keypad for your convenience to enter/exit into the suite at will, there is high speed Wi-Fi, HD cable tv, Kcup machine, heat/ac (indoor fireplace) also a firepit outsde ,rubber track and tennis courts literally in the back yard. 5miles away from Yale/nh and 5mins to Griffen Hospital and major highways great local restaurants

Guest favorite

A white Dutch door is framed by rustic wooden walls, showcasing a combination of horizontal and vertical planks. A small lantern hangs nearby, and a woven basket adorns the wall beside the door. A simple bench with a patterned cushion sits on the side.

Guesthouse in Southbury

4.93 out of 5 average rating, 345 reviews

Charming Guest Cottage with Modern Amenities

Private Guest House set on 5+ Acres, along with Historic Colonial Home. Bright and sunny and over looks pool and gardens (seasonal). Efficiency with Kitchen featuring 2 burner stove, Microwave, Under Counter Fridge/Freezer/Ice Maker, Dishwasher, Granite Counters. . Dining Area, Great Room w/ soaring ceilings, French Doors to private patio, hardwood floors. Loft with full-sized bed, and sofa can be a to Queen Size Sleeper. Full bath with extra-large shower. Dog friendly (approval needed).

A deck overlooking the Housatonic River features a circular table surrounded by four white chairs. A red umbrella stands upright, providing shade. The tranquil water reflects the greenery of the shoreline and the partly cloudy sky.

Bungalow in Seymour

4.7 out of 5 average rating, 136 reviews

Beautiful Waterfront on Housatonic River

Escape & enjoy the views of the mountains & the Housatonic River. Our waterfront little ranch house is great for a relaxing stay in Connecticut. The deck is right across the road down the stairs. Road can be busy at times. The fishing is epic, the sunset views are killer, & the kayaking is refreshing! You have private access to our deck & our 2 sit-in kayaks located across the road. Please be cautious when crossing the road. There are many fun activities/areas to visit nearby like Lake Zoar!

Top guest favorite

An expansive patio extends towards the shimmering waters of Long Island Sound, featuring lounge chairs and a dining table with an umbrella. Decorative planters and lanterns are arranged along the patio edge, complementing the serene waterfront view.

Apartment in Milford

4.97 out of 5 average rating, 596 reviews

Water front studio apartment with fireplace.

This is a beautifully appointed studio apartment located off the patio level of a water front home. Guests enjoy a large private patio over looking gorgeous sweeping views of Long Island Sound. A private entrance and off street parking. The amazing views and amenities make this space the perfect romantic getaway! Close to I95 and Metro North railroad. Ten minutes to great dining in downtown Milford. A true waterfront oasis! Come and experience this beautiful retreat! You won't be disappointed!

Top guest favorite

Apartment in Milford

4.98 out of 5 average rating, 124 reviews

The Pond Mill Retreat w/ 2 Bdrms & Pool

Catch up on a little work or simply unwind. Everything is waiting for you in this cozy, yet functional space surrounded by a beautiful wooded area with pond. Your private entrance accommodations include a finished, walk-out lower-level apartment (~730 sq ft) containing thoughtfully appointed bedrooms, living room, kitchen, and full bathroom. Experience solitude while enjoying the convenience to Rt 15, I-95, & Boston Post Rd destinations. And if you require assistance, we live right upstairs.

Guest favorite

A spacious living area is illuminated by natural light streaming through large windows. A comfortable gray sofa with decorative pillows faces a modern coffee table. A stylish area rug adds color, while a wall-mounted TV and decorative plants enhance the space.

Apartment in New Haven

4.95 out of 5 average rating, 384 reviews

Luxury Apt with Parking and Gym | Downtown at Yale

Nestled in the heart of New Haven’s historic downtown, our designer home is part of the city’s most prestigious new luxury complex, renowned for its unmatched amenities and design. Highlights: • Prime location just steps from Yale University • Immaculately cleaned before every stay • Complimentary coffee, plush linens, and premium toiletries • 24/7 state-of-the-art fitness center • Expansive rooftop terrace with grills and chic lounges • Over 700 sqft of bright and sophisticated living space

Top guest favorite

A comfortable living area is furnished with a beige sofa, center coffee table, and a TV on a wrought-iron stand. A rocking chair complements the space. Large windows allow natural light to fill the room, with access to a porch visible through the sliding doors.

Apartment in Southbury

4.95 out of 5 average rating, 44 reviews

New Apartment Centrally Located in Southbury

Keep it simple at this peaceful and centrally-located apartment. Recently renovated with all the essential amenities to make your stay just like home. Wi-Fi, washer, dryer, cooktop, fridge, oven, microwave, toaster, TV and Keurig are ready to make your stay pleasant. An outdoor porch is available for dining in warmer months. It includes one new queen bed plus sofa bed for one adult or two kids. Located just minutes from shopping and dining in downtown Southbury with easy access to i84

Top guest favorite

A tranquil view of Swan Lake is captured, surrounded by autumn foliage. Colorful outdoor chairs are positioned on a leaf-covered shore. Sunlight reflects off the calm water, creating a serene atmosphere that invites relaxation.

Home in Oxford

4.97 out of 5 average rating, 59 reviews

Lakefront Oasis - Getaway to this Oxford Treasure!

Relax with family and friends at this breathtaking lake front home. Peaceful setting with beautiful views of Swan Lake. Updated bedrooms, completely renovated bathrooms and all new kitchen appliances. A kayak and paddleboard await your next adventure. A brand new dock was installed for boating, fishing and swimming right from our backyard. Just a few minutes from the town center grocery store, restaurants, amusement parks, skiing and more. Dogs considered on a case by case basis!

Guest favorite

A cozy living space features a modern television mounted on a light wood console. A decorative plant adds a touch of greenery beside the TV. A wooden coffee table is positioned in the center, while a dining table with white chairs is visible in the background.

Condo in Hamden

4.87 out of 5 average rating, 134 reviews

Close to Yale Hospital, 1 bed apt, great location.

The offer specially dedicated to travel professionals working in the area of New Haven . Centrally located, best for 2 or one person, one queen bed, access to public transportation with bus stop just 1 min away take you straight to Yale in New Haven , Quinnipiac University, 20 min away to Tweed airport . Easy access to Merritt Parkway and I-91. Self check in with smart lock. No more than 5 min walking distance to Walgreen’s, Domino Pizza, Dunkin Donuts, Eli’s Brick Oven Pizza

Top guest favorite

A spacious deck features a round table surrounded by four cushioned chairs, covered by a large red umbrella. Lush greenery and landscaped gardens are visible in the background, creating a serene outdoor setting.

Cottage in Seymour

4.94 out of 5 average rating, 71 reviews

3 Acre Forest, 2 King Beds, Fireplace, BBQ & more

🛏️2 king, 2 twin, BBQ, fireplace, firepit, 1550 sqft entire house 🅿️🛜 Tucked away at the end of a quiet street, set on 3+ acres of lush wooded land, our home is the perfect blend of seclusion and convenience. With a forest as your backyard and RT34 one min away, you can easily balance your desire for nature and adventure with the need for easy travel and commuting, take a short hike into a forest (trails minutes away) and/or relax under the stars around a fire pit.

Top guest favorite

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

4.98 out of 5 average rating, 133 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.

Guest favorite

A cozy living room features a leather sofa, an exercise bike, and a central coffee table resting on a patterned rug. A shelf adorned with framed photographs lines the wall, complementing the warm color scheme.

Guest suite in Shelton

4.82 out of 5 average rating, 303 reviews

Super cozy 1 BR apt. own entrance, great loc.

Very quiet residential neighborhood, very clean, super cozy apartment with two bedrooms, living room; computer desk with work station, kitchenette (no stove), own bathroom, and amenities. 20 minutes away from Bridgeport, 15 minutes away from Yale, New Haven. Lakes in walking distance, Metro-North rail; 7 minutes, local shopping area 1 mile. Bus route in walking distance. Great neighborhood!! All are welcomed. Warm community.