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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

The kitchen showcases a spacious layout with white cabinetry and modern stainless steel appliances. A large island with seating for several guests is highlighted. Warm lighting from pendant fixtures complements the hardwood floors, while a cozy fireplace is visible in the adjacent living area.

Home in North Haven

5 out of 5 average rating, 152 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!

The exterior of a two-story beach cottage is visible, featuring a soft gray facade and a balcony on the upper level. Large windows illuminate the lower floor, surrounded by a well-kept lawn and garden. A decorative trellis adds character to the welcoming entryway.

Home in East Haven

4.89 out of 5 average rating, 238 reviews

Beach Cottage by the Sea

Beautiful 1920's beach cottage with beach access just across the street. Enjoy the sea breeze, ocean views, and sound of the waves lapping in this quaint home with unique architecture. Ten minutes to downtown New Haven and Yale for great places to eat, museums, and nightlife. Public beach and playground nearby. Warm and welcoming community. Master bedroom has vaulted ceilings and deck with views of the sea. Central Air, Cable TV, outdoor grill, plenty of parking. Enjoy this lovely home!

A tranquil lake scene is captured at sunrise, featuring a wooden dock extending into the water. Soft pink and orange hues reflect on the lake's surface, complementing the surrounding greenery. Two Adirondack chairs sit near a fire pit, inviting relaxation by the scenic view.

Home in East Haddam

4.93 out of 5 average rating, 246 reviews

Romantic Getaway at The Lake!

Beautiful year round getaway! Relax and have a glass of wine by the lake. Wake early to enjoy the sun rising directly over the lake with a fresh cup of coffee. Enjoy direct lake access on a trophy bass lake including a beautiful dock. Hot tub overlooking the water open year round. Enjoy dinner in front of beautiful gas fireplace. Amazing sunrises and colorful sunsets. The location and amenities make for a fantastic romantic getaway for two! Centrally located 30 minutes from the Mohegan Casino.

Top guest favorite

Home in East Shore

4.98 out of 5 average rating, 190 reviews

WaterviewsTakeWedding pics,CollegeTours Yale&Beach

PETS ALLOWED! Spectacular unobstructed Long Island Sound views year-round, out your front door along Pardee Seawall! This exceptional shore line property offers all new furniture & amenities. Minutes to wedding venues-perfect for getting dressed on your wedding day & taking photos literally right outside your door (props available). Near: Tweed NH Airport, beach, Yale University & Hosp, restaurants & museums. All new furniture, linens/towels, grill, fire pit, centralAC, WIFI. Onsite parking.

A view from the interior through a set of glass doors, showcasing tranquil waters and distant land. The scene highlights natural elements like tall grass along the shoreline, with a clear blue sky above.

Home in Milford

4.96 out of 5 average rating, 241 reviews

Designer Beach Retreat on Exclusive Cedar Beach

Welcome to your own slice of heaven! Enjoy dinner in your Chef's kitchen while watching one of the most radiant sunsets you will ever see. Stunning views from the private rear deck or snuggled on the couch inside the living room. Wade into Long Island Sound with semi-private beach access 250 feet away. The property is 5 doors down from the CT Audubon Society, known for its epic views and wildlife watching. The sunrises & sunsets are beautiful! 15 minutes to Yale. We can't wait to host you!

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, 122 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.

Home in Clinton

4.92 out of 5 average rating, 164 reviews

Amazing 2BR Riverfront Gem

Unwind at this happy getaway with an amazing river view, peaceful neighborhood, and in the heart of fall foliage and holiday scenes. The well-equipped kitchen overlooking the river is a pleasure for any cook. You will love to see our fairy-lit lawn, wishing well, chimenea, and charming décor. Only minutes to beaches, groceries, coffee shops, hiking trails and amazing CT scenery at every turn! Other favorites include Chamard Vineyard, Shopping Outlets, fantastic Restaurants, and lots more.

Top guest favorite

Home in Branford

4.98 out of 5 average rating, 182 reviews

“The Lighthouse” A Beach Cottage by the Sea!

Relax at this unique and tranquil getaway. Long Island Sound to the left, hiking trails to the right. Come kick your feet up at this quiet dead-end road. Enjoy all the modern amenities in this gem of a cottage community. Restaurants and nightlife are just a quick stroll away. Avoid roadside hotels and take a vacation for a night, week, or longer! Check in anytime and at your convenience!No keys to lose or to return! This property provides secure, keyless entry with an August Smart Lock!

A charming exterior view of the New England home features a covered porch with seating options. Black rocking chairs and a small side table are positioned on the patio, and well-maintained green grass surrounds the property, enhanced by the dappled sunlight filtering through nearby trees.

Home in Clinton

4.97 out of 5 average rating, 204 reviews

Waterside Beach Retreat

Beautiful New England period home steps from the beach on the Long Island Sound. Recently renovated from top to bottom with new kitchen and bathrooms, hardwood floors throughout. Idyllic location on quaint & quiet street. Hide away and relax or discover the many local attractions - water sports, fishing, winery, antique stores, scenic walks, premium outlet shopping are all on your doorstep. Ideally located off the I-95 halfway between NYC & Boston, both of which are a train ride away.

Top guest favorite

An open-concept living space is highlighted by light wood flooring and ample natural light. A comfortable seating area features a white sofa adorned with orange pillows. A dining table with black chairs is positioned near a cozy fireplace, enhancing the inviting ambiance.

5 out of 5 average rating, 136 reviews

Cozy Comforts!

Keep it simple at this peaceful and centrally-located place. Completely open concept and fully renovated. Country living yet just minutes to downtown Middletown and Wesleyan University. Come stay at our home away from home! We are about 20-25 min from the shoreline or travel in the other direction and you’ll be in our state’s capital, Hartford. We are only about 10-15 min from Wesleyan and downtown Middletown for shopping and great restaurants! You don’t want to miss this one!

A comfortable living area features a light-colored sofa accompanied by two lamps on side tables. A textured area rug lies beneath a coffee table, while natural light filters through multiple windows, creating a bright and open space. A dining area is visible in the background.

Home in Branford

4.94 out of 5 average rating, 118 reviews

Charming home, easy access to everything Branford

Full home, comfortable and very well equipped. Private fenced in backyard with patio dining area. Off-street (driveway) parking. Short Walk to the Shoreline Greenway trail. Less than a mile to downtown, parks, beaches, restaurants, marina, Stoney Creek Brewery. Near event venues, The Owenego and Pine Orchard club. Close to New Haven. Family(kid) Friendly home with private fenced in backyard with patio dining area. Equipped with Pack N Play, highchair, booster seat, etc

Home in Milford

4.96 out of 5 average rating, 110 reviews

Oceanfront Retreat: Modern Beach House

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.

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Popular amenities for Guilford house rentals

Free parking on premises

Air conditioning

House rentals with a pool

Top guest favorite

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, 208 reviews

Private Oasis W/Stunning Vinyard and Pool Views

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 The Hamptons

4.88 out of 5 average rating, 120 reviews

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

Home in Milford

4.83 out of 5 average rating, 104 reviews

Spacious 4 bedroom, oasis with ocean views galore

A welcoming living area features a light-colored tufted sofa and plush chairs arranged around a round coffee table. Natural light floods the space through large windows and decorative pendant lights hang from the ceiling. A green plant adds a touch of nature beside the cozy fireplace.

Home in The Hamptons

4.85 out of 5 average rating, 126 reviews

Sag Harbor Wonder, 3 bedroom 2 Bath & Heated Pool

Home in Montville

4.92 out of 5 average rating, 182 reviews

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

Top guest favorite

A cozy bedroom featuring a spacious bed dressed in soft linens is positioned against a light-colored wall. Natural light filters through two windows, casting gentle shadows on the warm wooden floor. A ceiling fan hangs overhead, and a mirror and chair add functional elements to the space.

Home in North Fork

4.98 out of 5 average rating, 179 reviews

Secluded Farmhouse - Studio Apartment Style Unit

Top guest favorite

A private country compound is showcased, featuring a main house with a classic white exterior and black shutters. A blossoming tree stands prominently in the foreground, surrounded by a well-maintained lawn and neatly trimmed hedges.

Home in The Hamptons

4.86 out of 5 average rating, 273 reviews

Exclusive Sag Harbor Compound

Home in Litchfield

4.93 out of 5 average rating, 194 reviews

Stunning Views, Bucolic Bliss in 1790s Farmhouse

Weekly house rentals

A red barn is nestled among tall green trees, with a stone wall visible in the foreground. The barn's exterior displays rustic charm, and a white horse silhouette can be seen on one side, enhancing the serene rural setting.

Home in North Branford

4.88 out of 5 average rating, 26 reviews

The Gait House at High Gait Farm

The historic Edwin Leete House is displayed, featuring a classic white exterior with dark green shutters. Lush greenery surrounds the entrance, and a clear path leads to the front of the house, framed by mature trees and well-maintained shrubbery.

Home in Guilford

4.97 out of 5 average rating, 36 reviews

Edwin Leete House

A charming two-story house is set on a green lawn, featuring white siding and dark green shutters. Gravel pathways lead to the entrance, and a small shed is visible to the side. Mature trees provide shade, enhancing the peaceful outdoor setting.

Home in Madison

4.86 out of 5 average rating, 42 reviews

Cozy beach cottage close to everthing

A charming ranch-style home is set within a lush green landscape, featuring a stone pathway leading to the front door. Vibrant pink azaleas and a deep red shrub add colorful accents to the front yard, framed by mature trees and shrubs.

Home in Guilford

4.9 out of 5 average rating, 59 reviews

The Davis House

A modern kitchen features a central island with three stools, surrounded by sleek countertops and essential appliances. Large windows and glass doors provide abundant natural light and a view of the outdoor area, seamlessly connecting the interior and exterior spaces.

Home in Clinton

4.88 out of 5 average rating, 26 reviews

Boulder Lake House Retreat

5 out of 5 average rating, 13 reviews

Quarry House: Mid-Century Modern

Home in Guilford

4.73 out of 5 average rating, 147 reviews

Purple Button Factory Sleeps 6 Walk to Town Green

The exterior of a cottage is displayed, featuring a warm orange front door framed by a simple porch with steps leading up. The building's shingles are a natural brown, complemented by multiple windows that invite daylight. Lush greenery surrounds the entrance, enhancing the welcoming appearance.

Home in Branford

5 out of 5 average rating, 5 reviews

5 Star Branford Cozy Cottage

Private house rentals

A collage showcases the various entertainment and relaxation areas. The top left features a game room with arcade machines and a dartboard. The top right highlights a manicured putting green. The bottom left displays the exterior of the home with outdoor seating, while the bottom right depicts a home gym with workout equipment against a bright orange wall.

Home in Westbrook

5 out of 5 average rating, 6 reviews

Beachside Bliss w/ Game Room, Gym & Golf Green

Top guest favorite

A charming colonial home with a vibrant exterior is surrounded by lush greenery and well-maintained shrubs. The inviting front porch features steps leading to a yellow entryway, while sunlight filters through the trees, enhancing the warmth of the scene.

Home in Wallingford

5 out of 5 average rating, 66 reviews

New England Charmer

A beachfront retreat is depicted, showcasing a light-colored house with a large deck facing the water. The sandy beach extends along the property, with neighboring houses visible on both sides. Gentle waves lap at the shore, creating a serene coastal setting.

Home in Clinton

5 out of 5 average rating, 35 reviews

Soundscape Beachfront House!

The exterior of a charming house is presented with natural wood siding and a steeply pitched roof. Lush greenery surrounds the property, including manicured bushes and a white picket fence that encloses the front yard. A large tree provides shade, enhancing the inviting appearance.

Home in Hotchkiss Grove

4.59 out of 5 average rating, 39 reviews

Beautiful 3br Shoreline Home - Steps to Beach

Top guest favorite

An outdoor deck is illuminated by soft lights, showcasing a private hot tub with blue lighting. A wooden picnic table with an umbrella and a stainless steel BBQ grill are visible, providing a comfortable area for relaxation and dining. The surrounding trees create a tranquil atmosphere.

Home in East Shore

4.99 out of 5 average rating, 84 reviews

3BD w/ Hot Tub Close 2 Beach+Free EV charge

A dining area features a farmhouse-style table set for eight, adorned with blue and white plates and decorative tapered candle holders. Light fills the space from wrap-around windows, while a cozy rug adds warmth to the hardwood floor. A rustic chair complements the table's design.

Home in Guilford

4.94 out of 5 average rating, 17 reviews

River's Edge

The modern villa is depicted from an aerial view, showcasing its unique architectural design. The exterior features soft curves and a light-colored façade, harmoniously blending with the surrounding greenery. A wooden walkway leads to the entrance, emphasizing its connection to the natural landscape.

Home in Deep River

4.87 out of 5 average rating, 82 reviews

Starship River Views: Dates Just Newly Released

Top guest favorite

Home in East Hampton

5 out of 5 average rating, 36 reviews

CT River Retreat - Modern Home with CT River Views

Quick stats about house rentals in Guilford

Total rentals
60 properties
Total number of reviews
2.9K 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