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House vacation rentals in Guilford

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Top-rated house rentals in Guilford

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Top guest favorite

A charming single-story house features a classic shingle exterior with a brick chimney. A spacious front deck is bordered by white railings and overlooks a manicured lawn surrounded by trees. Soft sunlight filters through the leaves, enhancing the serene setting.

Home in East Hampton

4.95 out of 5 average rating, 230 reviews

Private beach, fully updated cottage, on 2 acres.

Each the special magic that only the Hamptons offer—historic charm, a rural atmosphere, white sandy beaches and a relaxed lifestyle—while staying in this light-filled three-story cottage. Tucked away on a beautiful 2.2-acre wooded lot, this bayside oasis offers a tranquil retreat, with deer sightings, private beach access, stunning view and picture-perfect sunsets. A short drive to the beaches and town, quick trips to nearby shops, market stands, restaurants, museums and Jackson Pollack house.

The exterior view showcases a bright, newly constructed home with white siding and a stone accent at the lower level. A spacious porch with seating is visible, along with a well-maintained lawn and a fenced yard, creating a welcoming entrance.

Home in Fairfield

5 out of 5 average rating, 8 reviews

Newly built twin beach house within steps to beach

Keep it simple at this peaceful and centrally-located home. Newly built in 2019! Premier beach living at its finest. Steps to Fairfield’s beaches and less than a mile to downtown restaurants, shops, and bars. Fenced backyard. Central air throughout. Decks off the front and back with a Weber grill. Furnished with luxury furniture, sheets, comforters, and pillows. Smart TVs in every bedroom and living room. Tesla charging station at the house. Identical home next door available for larger bookings

Top guest favorite

A stylish dining area is highlighted by a round table paired with modern chairs beneath a vibrant artwork. Natural light filters through large windows, providing a view of the outdoors. A cabinet with decorative items adds character to the inviting space.

Home in North Fork

5 out of 5 average rating, 9 reviews

Stylish Beach Getaway: pool & walking location

Perfectly located within walking distance to shops, beaches, and restaurants, our designer home offers comfort, luxury amenities, and privacy. Interested in a long term rental? Message us! Enjoy a beautifully landscaped backyard with pool, chefs kitchen for hosting, and nearby beach farms & wineries. Bedrooms boast organic linens and bathrooms offer Bathing Culture products. Kitchen is stocked with local organic pantry staples and stainless steel appliances to cook or grill on the patio.

Top guest favorite

The exterior of a charming two-story house is presented, featuring light siding and dark shutters. Window boxes adorned with blue flowers are visible. A small porch with a door leads into the home, accompanied by a stone pathway and neatly landscaped shrubs.

Home in Old Saybrook

4.97 out of 5 average rating, 121 reviews

Year Round Beach House in Old Saybrook, CT.- Pets

Our Beautiful Home is Located in Saybrook Manor Association and only a short walk to the beach . We have 4 Bedrooms that can accomadate 8 people,pull out couch,2 bathrooms, a Dining Room,Kitchen, and Spacious Living room.Our Yard is fenced in for your privacy & pets.Our home comes with many ammenities such as movies,games,kayaks, Clamming &Crabbing tools,Bikes,Floats & Beach Chairs.We have a beautiful backyard to enjoy games,barbecue or just to relax & unwind.Enjoy our beautiful & quaint beach

The entrance of the home is framed by white, picket fencing and vibrant floral landscaping. A covered porch with classic columns supports a welcoming entrance. The door features decorative glass elements, providing an inviting touch to the exterior.

Home in North Fork

4.98 out of 5 average rating, 100 reviews

Designer's Dream - Charming Boathouse

An architect's and interior decorator's dream home! This home is a historic boathouse built in the late 1890's, and recently & lovingly fully renovated and restored. In the middle of Greenport Village - walking distance to train station, Jitney stop, and Shelter Island Ferry as well as the best North Fork restaurants, vineyards, bars, and beaches. Two bedroom home with ground floor fireplace, outdoor shower (not enclosed), and beautifully landscaped outside patio w/grilling & dining areas.

A waterfront home with a unique tower design is reflected in the calm waters of Bantam Lake. The house features multiple outdoor decks, large windows, and is surrounded by trees, providing a serene setting. A private dock extends into the lake, inviting exploration.

4.87 out of 5 average rating, 149 reviews

Bantam Lake Waterfront Retreat with Private Beach

Waterfront home on Bantam Lake, 3BR/2BA. Relax on the deck, enjoy the sunrise, swim at your private beach. Kayaks available for use (4); bring your boat or jet ski. Minutes away from hiking, snow skiing, vineyards, biking, and so much more. The area offers great restaurants and family friendly activities that are minutes away. BBQ on the gas grill, enjoy the fire pit on the beach. House is great for couples, individuals & families. Please check first if you plan to bring a boat. 7 maximum.

A charming two-story blue house is framed by lush greenery and a manicured lawn. Soft light emanates from the yellow windows, creating a welcoming glow. A red door stands as a vibrant focal point, inviting guests into the comfortable space.

Home in Litchfield

4.84 out of 5 average rating, 373 reviews

Rustic - Modern - Hot Tub - Mohawk Mountain - BBQ

Enjoy the comfort of home with air conditioning, heating, dedicated workspace, TV, and Wi-Fi. Cook your meals in the fully-stocked kitchen with all the essentials. Pamper yourself in the private bathtub or shower with provided body soap, shampoo and conditioner. Relax in the hot tub or lounge in the backyard with an outdoor dining area, bbq, patio, and fire pit. 3 Min - Litchfield Town 4 Min - Arethusa Dairy farm 5 Min - White Memorial Conservation Center 16 Min - Mohawk Mountain Ski Area

A balcony view captures a serene beachfront scene at sunset, with gentle waves lapping at the sandy shore. A detailed metal chair is positioned on the deck, providing a quiet spot to enjoy the tranquil waters and cloudy sky.

Home in East Lyme

4.96 out of 5 average rating, 186 reviews

Beachfront Paradise

Beautiful beachfront home available weekly in season (6/21/25-9/6/25) and nightly (2 night min.) off season. Step out the door and into the sand. Sit on the porch and watch sailboat races from Niantic Bay Yacht Club just steps away. Close to downtown Niantic with restaurants, shops, movie theatre, etc. 18 miles from Mohegan Sun Casino. Attractions within 1/2 hour: Beautiful Mystic, CT, several vineyards, Harkness State Park, Eugene O'Neill Theatre, U.S. Coast Guard Academy, golf courses.

A charming stone exterior is visible, featuring a private entrance with a sliding glass door. The path is made of stone, surrounded by a well-maintained lawn. In the background, sitting areas and greenery are discernible, enhancing a serene outdoor experience.

Home in Clinton

4.93 out of 5 average rating, 135 reviews

Amazing 2BR Riverfront Gem

Unwind at this happy getaway on the river. Comfy cozy with amazing views. Come experience the charm of New England in any season! The well-equipped, intimate kitchen overlooking the river is a pleasure for any cook. You will love our fairy-lit lawn, wishing well, and warm charming décor. Only minutes to groceries, coffee shops, beaches and amazing CT scenery. Other favorites include Chamard Vineyard, Shopping Outlets, Essex Steam Train, fantastic Restaurants with music, and lots more!

Top guest favorite

A covered porch area features woven seating with bright green cushions and a chaise lounge. The wooden railing complements the light green siding of the house. Potted plants add color, while light filters through the oversized windows, providing a warm and welcoming atmosphere.

Home in Milford

5 out of 5 average rating, 101 reviews

Steps2Beach, Fish Pond w/Tropical Backyard Oasis!

🌴Steps from Walnut Beach & Silver Sands State Park, this guest-favorite escape offers a tropical backyard oasis with a cascading fish pond, multiple lounges, & a seasonal palm tree. Explore the scenic coastline, build sandcastles, or enjoy a day of kite flying. Inside, relax in luxury with a gourmet kitchen, elegant furnishings, & modern amenities. Just 90 minutes from NYC & 15 from New Haven, it’s the perfect retreat for beach days, nature adventures, & coastal charm!

The front exterior of the home is framed by lush greenery and a flower-lined pathway made of stone. Two trees add natural shade, while a charming yellow door welcomes guests. A fenced yard and gravel accents enhance the inviting entrance.

Home in North Fork

4.94 out of 5 average rating, 108 reviews

Maritime Village Getaway with Backyard

Well located Greenport 3 bedroom, 2 bath home. Historic renovated private home with modern furnishings and updated appliances and finishings. Patio and yard with outdoor shower, fire pit, and yard. Central AC and heat. Properly licensed as a rental with Greenport Village and Suffolk County. I now add the airbnb fees and local and state taxes onto the listing. If you have questions about this please reach out. Not sure how transparent the fee structure is for guests.

A dining room table with eight chairs is set beneath ambient lighting. The room opens to a cozy living area featuring a comfortable sofa and blue curtains. A doorway leads to a well-lit kitchen, enhancing the home's spacious layout.

Home in New London

4.95 out of 5 average rating, 133 reviews

House in NL near CGA, Sub Base, Mohegan Casino

House is located in New London CT. Off I95 near Coast Guard Academy 3 mins, Connecticut College 4 mins, Mitchell 11 mins, Navy Base 9 mins,Yale L&M Hospital 10 mins, Branford House Avery Point 15 mins, Ocean Beach 16 mins, Millstone 19 mins, Mohegan 16 mins, Foxwoods 24 mins, Electric Boat 9 mins. Enjoy private house with full kitchen, and dining room for family get together. 20% Discount weekly stay. 35% on monthly stay

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Popular amenities for Guilford house rentals

Free parking on premises

Air conditioning

House rentals with a pool

A two-story house showcases a charming exterior with blue shutters and a welcoming red door. The landscaped front yard features vibrant flower beds and manicured greenery, providing a serene setting against a clear blue sky.

Home in North Fork

4.97 out of 5 average rating, 203 reviews

Private Oasis W/Stunning Vinyard and Pool Views

The outdoor area is highlighted by a heated pool surrounded by lounge chairs and a well-maintained garden featuring a mix of hedges and trees. A spa is situated near the pool, with a stone patio providing additional seating under a blue sky dotted with clouds.

Home in Litchfield

4.82 out of 5 average rating, 105 reviews

The Getaway-HOST & Co.

Top guest favorite

A light-filled living area features a neutral-colored sofa alongside a blue couch, with decorative pillows adding subtle color. A wooden coffee table rests in front, and large windows with bamboo shades allow natural light to brighten the space.

Home in North Fork

4.88 out of 5 average rating, 123 reviews

The Perfect North Fork Escape

A light-filled dining area features a round wooden table surrounded by four white chairs. French doors open to a lush outdoor space, and the wood-beamed ceiling adds a rustic touch. The adjacent kitchen with white cabinetry is partially visible, enhancing the open feel.

Home in East Hampton

4.88 out of 5 average rating, 107 reviews

4 BD w/ Heated Pool in E Hampton, Fully Furnished

A modern home is showcased with a unique angular design, featuring a combination of wood and glass. The surrounding lawn is spacious and well-maintained, with natural landscaping, including grasses and a small tree, contributing to the serene outdoor setting.

Home in East Hampton

4.88 out of 5 average rating, 109 reviews

Modern East Hampton Home w/ Heated Saltwater Pool

Top guest favorite

An inviting outdoor area features a heated pool surrounded by a spacious patio. Comfortable lounge chairs are neatly arranged on the side, with umbrellas providing shade. Lush greenery and trees create a serene backdrop, enhancing the tranquil setting of the Pool House.

Home in Cheshire

5 out of 5 average rating, 132 reviews

Pool House

Top guest favorite

The outdoor area features a large in-ground pool surrounded by a fence, with lounge chairs and shaded umbrellas. A spacious wooden deck is visible, along with seating and a small shed. The lush greenery of the backyard complements the serene setting.

4.97 out of 5 average rating, 200 reviews

Garden Level Suite with Beautiful Pool

Home in Montville

4.94 out of 5 average rating, 151 reviews

Hot Tub~Pool~Game Room~Fire Pit~BBQ~Casinos

Weekly house rentals

A wooden pathway leads through sandy terrain, flanked by low vegetation. The scene is set against a clear blue sky, creating a serene atmosphere that guides visitors toward the shoreline.

Home in Westbrook

4.86 out of 5 average rating, 194 reviews

Family-Friendly Cottage by The Shore

A charming historic bungalow is presented with a shingle exterior and turquoise accents. The entrance is framed by flower boxes, and brick paving extends to the driveway. Lush greenery surrounds the property, while clear blue skies complement the inviting facade.

Home in North Fork

4.98 out of 5 average rating, 187 reviews

Nofo Bungalow-In The Heart of Greenport Village

Home in North Fork

4.97 out of 5 average rating, 254 reviews

The Greenport Bungalow

Home in Washington

5 out of 5 average rating, 6 reviews

Zoom In Lux 5*Washington "Calhoun 4BR" PoshPadsCT

A spacious outdoor deck features woven seating and a glass-topped table, overlooking the tranquil water. Sunlight casts shadows on the wooden surface, creating a relaxing atmosphere. Nearby, the waterfront and boats are visible, enhancing the coastal setting.

4.95 out of 5 average rating, 192 reviews

True Ocean Front Vacationing - Groton/Mystic

A bright bedroom is presented with a spacious bed, accented by a light-colored comforter. A wooden dresser and a bedside lamp add to the decor. Natural light streams through two windows with light curtains, providing a serene atmosphere.

Home in New Britain

4.89 out of 5 average rating, 104 reviews

5•Star CapeCodStyle Gem with Bedroom on the Main

Home in Madison

4.87 out of 5 average rating, 23 reviews

Historic Beachside Glamour

A bright living area features a large flat-screen TV mounted on a white console. Two colorful armchairs and a brown leather couch surround a wooden coffee table, all set on a blue area rug. Light streams in through a window, enhancing the cozy atmosphere.

Home in East Hampton

4.92 out of 5 average rating, 93 reviews

Clean private home near Lake Pocotopaug!

Private house rentals

The exterior of a single-story home is set among lush greenery, featuring a varied facade with shingle and clapboard elements. Symmetrical landscaping includes neatly trimmed shrubs and a spacious lawn. A pathway leads to the front door, framed by tall trees providing natural shade.

Home in Shelter Island

4.88 out of 5 average rating, 26 reviews

Peaceful and Private 3 bedroom home in the woods

The exterior of the house features a multi-level deck and abundant autumn foliage in vibrant colors covering the ground. Two decorative benches are situated in the foreground, offering a tranquil spot to enjoy the surrounding nature.

Home in Chester

4.98 out of 5 average rating, 209 reviews

Stunning Artisan Waterfall Escape, Walk Downtown

The exterior of a two-story single-family home is depicted, featuring beige siding and a centered front door. Lush green grass surrounds the walkway leading to the entrance, with a mailbox positioned at the pathway. A nearby tree and hedges provide additional greenery.

Home in East Haven

4.89 out of 5 average rating, 101 reviews

Welcome To Piper's Rest

A charming red farmhouse exterior is seen, featuring large glass doors leading to a spacious deck. Colorful chairs are arranged on the deck, surrounded by lush green grass and trees, creating an inviting outdoor space. The clear sky enhances the overall bright appearance.

Home in Shelter Island

4.82 out of 5 average rating, 11 reviews

RedHouse with Sprawling Backyard & Hot Tub

The white estate is framed by bare trees, showcasing a combination of traditional architecture and natural surroundings. A serene lawn is visible in the foreground, with stone walls adding rustic charm. Soft lighting illuminates the porch, creating a welcoming atmosphere.

Home in East Haddam

5 out of 5 average rating, 25 reviews

Elegant Countryside Estate

A charming beachside home is showcased, featuring a wrap-around porch with seating. The sandy beachfront extends along the water's edge, and a clear blue sky overhead enhances the coastal atmosphere. Nearby houses are visible, offering a sense of community along the shore.

Home in Woodmont

4.98 out of 5 average rating, 43 reviews

Beachfront paradise- come, stay, relax!

A modern kitchen features sleek black cabinetry and stainless steel appliances. A large island with bar seating is centered, adorned with a vase of fresh flowers. Natural light floods in through the windows, and a sliding glass door leads to the outdoor deck.

4.92 out of 5 average rating, 330 reviews

Stunning, peaceful and private home

Top guest favorite

A charming beach cottage is showcased, featuring a light-colored exterior and a welcoming front porch adorned with potted plants. Large windows allow natural light to flood the interior. The surrounding area includes a gravel driveway and mature trees with autumn foliage.

Home in Woodmont

4.92 out of 5 average rating, 254 reviews

Bright and Breezy Cottage by the Sea

Quick stats about house rentals in Guilford

Total rentals
60 properties
Total number of reviews
2.8K reviews
Family-friendly rentals
40 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
30 properties have a dedicated workspace
Wifi availability
60 properties include access to wifi

Destinations to explore