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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, 236 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 spacious deck overlooks the shimmering waters of Long Island Sound, offering both lounge seating and a dining area. The railing lines the edge of the deck, enhancing views of the tranquil waves and bright blue sky, creating a serene waterfront atmosphere.

Home in East Haven

4.92 out of 5 average rating, 100 reviews

Luxury Beachfront Retreat - Modern Shoreline Villa

Welcome to luxury living and the peaceful beach vibes on Cosey Beach! Jutting out into Long Island Sound, guests will enjoy unparalleled waterfront living as waves break directly under your luxury vacation villa. Breathtaking sunrises and sunsets abound from the main living spaces and multiple decks. Descend to your private beach to use one of the provided kayaks or paddle boards, or wander down the street to family friendly fun, including splash pad, casual restaurants, and ice cream counter.

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

4.92 out of 5 average rating, 239 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.

A sandy pathway leads to a private beach, marked by a wooden fence with a sign reading 'PRIVATE BEACH.' A tranquil water view features a distant island and gentle waves under a partly cloudy sky.

Home in Branford

4.87 out of 5 average rating, 202 reviews

Gorgeous 4BR Beach House - 250 ft to private beach

Enjoy our newly remodeled 4 bedroom home with water views and a 250 foot walk to Limewood Beach with private beach access. Our home is a 5 minute walk to 5 restaurants and bars, and a 5 minute Uber ride to the train station. Enjoy swimming and boating in the warmer months, or take a stroll along the beach and collect shells and sea glass all year round. No matter which time of year you visit, you will appreciate the tranquility of the ocean and will feel completely relaxed during your stay.

An aerial view showcases a coastal neighborhood with homes situated along a sandy beach. Vibrant blue waters and marshlands surround the area, emphasizing its seaside location. The arrow points to the property's location within the community, illustrating proximity to the beach.

Home in Milford

4.96 out of 5 average rating, 236 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!

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

4.95 out of 5 average rating, 121 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

A serene view of the Long Island Sound showcases several sailboats gently drifting on the blue water. The scene is framed by a simple fence and grassy area, with a clear blue sky above, creating a peaceful coastal atmosphere.

Home in New Haven

4.98 out of 5 average rating, 189 reviews

WaterviewsTakeWedding pics,CollegeTours Yale&Beach

Spectacular unobstructed Long Island Sound views to enjoy year-round out your front door along Pardee Seawall! This exceptional shore line property offers all new furniture & amenities. Minutes from 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 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

4.92 out of 5 average rating, 160 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

An open-concept kitchen and living space features modern appliances and a wood-topped island with seating for three. Light cabinets and blue walls create a bright environment, while a hallway visible in the background leads to the entrance of the cottage.

Home in Branford

4.98 out of 5 average rating, 178 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!

Top guest favorite

A historic New England home features a classic white exterior with multiple windows. Surrounding greenery includes mature trees and a well-maintained lawn. The side of the house provides a glimpse of a separate structure, enhancing the spacious outdoor area.

Home in Clinton

4.97 out of 5 average rating, 203 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 features light-colored wood flooring and a cozy seating area with a white couch and wooden coffee table. A small dining table is positioned nearby, while a stylish staircase leads to an upper level. A television is mounted on the wall, adding to the modern atmosphere.

5 out of 5 average rating, 134 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!

Vacation rentals for every style

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Popular amenities for Guilford house rentals

Free parking on premises

Air conditioning

House rentals with a pool

An above-ground pool is shown, featuring clear blue water surrounded by a sturdy gray frame. Lush greenery forms the backdrop, suggesting a private outdoor space. Sunlight creates gentle ripples on the water's surface, inviting relaxation and enjoyment during warmer months.

Home in Montville

4.92 out of 5 average rating, 290 reviews

Casino Wine Down House

Top guest favorite

Home in North Fork

4.97 out of 5 average rating, 207 reviews

Private Oasis W/Stunning Vinyard and Pool Views

A spacious backyard features a heated swimming pool surrounded by a sun deck, adorned with loungers. Lush greenery and trees provide a natural backdrop to the inviting setting, while a charming house is visible in the distance.

Home in East Hampton

4.87 out of 5 average rating, 118 reviews

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

A modern home is set in a lush green environment, showcasing a spacious heated saltwater pool surrounded by a stone patio. Relaxing lounge chairs are placed alongside the pool, and the house features large windows that reflect the tranquility of the yard.

Home in East Hampton

4.88 out of 5 average rating, 111 reviews

Modern East Hampton Home w/ Heated Saltwater Pool

A spacious outdoor area features a heated pool surrounded by a stone patio. Lounge chairs are placed under umbrellas for shade, and the well-maintained lawn is bordered by lush hedges and flowering plants. The modern home is visible in the background.

Home in East Hampton

4.95 out of 5 average rating, 104 reviews

Marvelous 4 Bed East Hampton home w Heated Pool

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, 176 reviews

Secluded Farmhouse - Studio Apartment Style Unit

Top guest favorite

An outdoor patio features multiple wooden lounge chairs arranged around a central fire pit. A gunite pool with clear water reflects the surrounding greenery. The main house, visible in the background, showcases a classic design with white siding and large windows.

Home in Sag Harbor

4.86 out of 5 average rating, 270 reviews

Exclusive Sag Harbor Compound

Top guest favorite

A spacious pool area features a crystal-clear swimming pool surrounded by a wooden deck. Colorful sun loungers are arranged neatly, accompanied by large umbrellas offering shade. Lush greenery is visible in the background, enhancing the tranquil outdoor setting.

Home in East Hampton

4.93 out of 5 average rating, 158 reviews

Large heated pool, games room, near private beach

Weekly house rentals

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

Top guest favorite

A covered patio area is visible, featuring a spacious seating arrangement with light-colored cushions. A brick chimney rises from the side of the home, surrounded by well-manicured grass and green shrubs. The peaceful setting is complemented by the presence of trees in the background.

Home in Madison

5 out of 5 average rating, 23 reviews

Beach Home & Garden Paradise

The inviting entrance of the ranch-style home features a warm red door set beneath a covered porch, framed by a rocking chair. Lush greenery surrounds the doorway, with colorful flowers and shrubs adding vibrancy to the front yard. A stone path leads from the driveway to the entrance.

Home in Guilford

4.9 out of 5 average rating, 58 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, 25 reviews

Boulder Lake House Retreat

Top guest favorite

Home in Madison

5 out of 5 average rating, 35 reviews

Stylish Modern Home, 4-Bedroom, Madison CT

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 Branford

4.59 out of 5 average rating, 39 reviews

Beautiful 3br Shoreline Home - Steps to Beach

A spacious living area features natural wood beams and light-colored furnishings. A large plant sits in a ceramic vase on a round table, while a comfortable sofa arrangement is placed around a central coffee table. Multiple windows provide ample natural light.

4.97 out of 5 average rating, 36 reviews

The Farmhouse Stay

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

Private house rentals

A charming two-story farmhouse is depicted with a white exterior and a brown-shingled roof. The front porch is furnished with two chairs and includes a decorative lantern. Lush green grass surrounds the house, providing a serene setting amidst the trees.

Home in North Branford

4.88 out of 5 average rating, 25 reviews

The Gait House at High Gait Farm

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, 3 reviews

Beachside Bliss w/ Game Room, Gym & Golf Green

A serene coastal scene displays a sandy beach curving into a calm cove, bordered by greenery. Kayaks and paddleboards are neatly lined up on the sand, ready for use. The tranquil water reflects the surrounding landscape and offers a backdrop of distant homes along the shoreline.

Home in Branford

4.87 out of 5 average rating, 15 reviews

Calm Private Beach | less than 2h from NYC

Top guest favorite

A spacious living room features a large sectional couch adorned with colorful pillows, next to a smaller armchair. Natural light floods through wide windows framed by vibrant curtains. A wooden coffee table sits in the center, with art pieces displayed on the walls and a guitar nearby.

Home in Westville

5 out of 5 average rating, 86 reviews

Westville Schoolhouse by Stephanie and Damian

An aerial view of Quarry House showcases its Mid-Century Modern design surrounded by lush trees. The expansive wraparound deck with seating provides a space for relaxation, while the home's large windows reflect the evening light, seamlessly blending indoor and outdoor living.

5 out of 5 average rating, 13 reviews

Quarry House: Mid-Century Modern

A beach scene features several wooden benches arranged on a grassy area, providing views of the sandy shore and calm water. A sheltered picnic area sits nearby, along with playground equipment and scattered leaves on the ground. Soft clouds drift across a clear blue sky.

Home in East Haven

4.91 out of 5 average rating, 69 reviews

Cosey Beach•6ft Tall Fenced in Backyard

A tranquil view of a private beach stretches along the coastline, where gentle waves lap against the smooth sand. Soft clouds dot the blue sky, while beach houses stand in the background, providing a serene coastal ambiance.

Home in East Haven

4.96 out of 5 average rating, 50 reviews

Direct Beachfront Modern Cottage on Private Beach

A modern kitchen features dark cabinetry and white countertops. Bar seating is provided by four rattan chairs at the island. Stainless steel appliances include a refrigerator and stove, with a coffee maker and sink visible. Light fills the space through a nearby window.

Home in Madison

4.89 out of 5 average rating, 53 reviews

Coastal getaway with water views in every room

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

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