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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 modern kitchen space features a large central island with seating for six. Sleek white cabinetry and stainless steel appliances complement the warm wood flooring. A cozy fireplace is situated in the corner, providing an inviting spot for relaxation.

Home in North Haven

5 out of 5 average rating, 146 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, 228 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

4.94 out of 5 average rating, 224 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 serene outdoor space is presented, featuring two black adirondack chairs positioned on a well-maintained lawn. Colorful flower pots are placed on either side of a small table, with lush greenery surrounding the area and a tranquil lake visible in the background.

Home in Westbrook

4.79 out of 5 average rating, 125 reviews

The Dragon Fly Garden

The phrase "nestled in nature” is the best way to describe the dragonfly's den. Sitting on the trail head to over 1,000 acres of the Cocaponsette State Forest across from Messerschmidt pond and just three miles from the winding salt water marsh water way you won't find a better mix of activities. Golf & boating are just moments away. Mountain biking & Trail running off the property. This country cottage boasts lake views, wildlife and wandering trails to loose yourself within. 1GB internet

A serene garden space features lush green foliage and vibrant pink flowers, with a rustic wooden chair positioned to overlook a gentle waterfall. The surrounding trees provide a natural canopy, creating a peaceful atmosphere for relaxation.

Home in Chester

4.98 out of 5 average rating, 211 reviews

Stunning Artisan Waterfall Escape, Walk Downtown

Rated one of the top 70 airbnb's near NYC on the online mag "Curbed". Featured on EarthxTV "House of What" series. Over 10 years of craftsmanship went into creating a work of art using more than 80% recycled materials. Known locally as "The Recycle House," this is the perfect place to stay to explore shops and galleries in downtown Chester - just steps away. When you are done shopping, come back and relax in the zen-like garden overlooking a waterfall or curl up inside by the fire place.

Top guest favorite

A cozy living area is presented, featuring a spacious gray sofa and two vibrant orange chairs. A coffee table rests atop a colorful area rug, with natural light filtering in through large windows. Green foliage is visible outside, enhancing the welcoming ambiance.

Home in New Haven

4.99 out of 5 average rating, 301 reviews

Q River House - 2 bdrm, minutes from Yale/Downtown

Q River House: newly remodeled two bedroom home in the historic Fair Haven neighborhood, conveniently located minutes from downtown New Haven and Yale. Take in river views with your morning coffee on the front porch and relax on the large and private back deck. Enjoy one of the city’s many fine restaurants or cook for yourself in the fully appointed modern kitchen. This riverfront home has been lovingly decorated with attention to style and comfort, and features off-street driveway parking.

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, 225 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

4.95 out of 5 average rating, 118 reviews

Connecticut Chalet - Private Pond, Firepit, Views!

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.

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

4.94 out of 5 average rating, 145 reviews

Amazing 2BR Riverfront Gem

Unwind at this happy getaway on the river. Comfy cozy with amazing views of River. Convenient to beaches, and includes free pass to the Clinton Town Beach! The well-equipped, intimate kitchen overlooking the river is a pleasure for any cook. You will love our fairy-lit lawn, wishing well, chimenea, and charming décor. Only minutes to groceries, coffee shops and amazing CT scenery! Other favorites include Chamard Vineyard, Shopping Outlets, fantastic Restaurants with music, 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, 160 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 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, 194 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, 129 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

Home in Stonington

4.87 out of 5 average rating, 107 reviews

Homestead Near Mystic, Casinos & Beaches

Top guest favorite

Home in North Fork

4.97 out of 5 average rating, 206 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

4.88 out of 5 average rating, 111 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, 111 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, 135 reviews

Pool House

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

4.97 out of 5 average rating, 156 reviews

Secluded Farmhouse - Studio Apartment Style Unit

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, 154 reviews

Large heated pool, games room, near private beach

A private outdoor pool is surrounded by lush green grass and shaded by tall trees. The water appears clear and inviting, with blue tiles lining the edges. A lounge chair and a poolside seating area are positioned nearby, offering a tranquil space for relaxation.

Home in North Fork

4.96 out of 5 average rating, 112 reviews

Quiet, Upscale Retreat by the Beach with NEW Pool

Weekly 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

4.92 out of 5 average rating, 12 reviews

The Gait House at High Gait Farm

A scenic view of a sandy beach lined with boats in the calm water, framed by greenery and colorful flowers. The ocean reflects the clear blue sky, creating a peaceful atmosphere along the shoreline.

Home in Branford

5 out of 5 average rating, 55 reviews

Beach House in Private Community on LI Sound

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, 21 reviews

Beach Home & Garden Paradise

A shingle style home is showcased, featuring a distinctive chimney. The exterior is finished with light-colored shingles, complemented by greenery surrounding the base. Tall trees can be seen in the background under a partly cloudy sky.

Home in Branford

4.82 out of 5 average rating, 73 reviews

Beautiful 3 bedroom shoreline house

Top guest favorite

An outdoor seating area is shown with comfortable chairs and a fire pit surrounded by paved stones. A well-maintained lawn and tall evergreen trees provide privacy, while large glass doors lead into the house, inviting natural light into the space.

Home in New Haven

5 out of 5 average rating, 54 reviews

Private 6-Bed House w/ King Bd, Groups & Families

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, 31 reviews

The Farmhouse Stay

Top guest favorite

A gated entrance leads to a sandy path towards the beach, with a serene view of the water. A small island can be seen in the distance, framed by a clear blue sky. Surrounding vegetation adds a touch of greenery to the scene.

Home in Branford

4.98 out of 5 average rating, 41 reviews

The Eagle- Private Beach

Top guest favorite

A comfortable living area features a gray sofa positioned around a low coffee table. A television rests on a media console against the wall, with natural light streaming through two windows that overlook greenery outside.

5 out of 5 average rating, 25 reviews

The Doll House

Private 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

4.83 out of 5 average rating, 36 reviews

Cozy beach cottage close to everthing

A comfortable living room features a pink sectional sofa arranged in a L-shape, accompanied by a light-colored armchair with a small side table. A colorful area rug adds warmth, while large windows adorned with sheer curtains provide natural light. Shelving displays decorative items.

Home in New Haven

5 out of 5 average rating, 14 reviews

The Jewel of The Cove - Historic Coastal Retreat

Top guest favorite

A spacious living area features a white sectional sofa and leather armchairs, arranged to face large glass doors that provide views of the beach. Natural light fills the room, highlighting warm wood paneling and a cozy, inviting atmosphere. A dining table is visible in the background.

Home in North Fork

5 out of 5 average rating, 13 reviews

Kayaks ~ Bikes ~ Boards ~ 6mins> Greenport ~ 55"TV

A spacious bedroom is highlighted with a large bed, dressed in neutral linens, surrounded by light walls and wooden flooring. A cozy area rug adds texture. A serene view is available through a nearby window. In the lower section, a pet is seen relaxing on vibrant green grass.

Home in North Haven

4.83 out of 5 average rating, 36 reviews

Trail-side Haven Retreat! Pet friendly

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

4.95 out of 5 average rating, 41 reviews

Direct Beachfront Modern Cottage on Private Beach

Top guest favorite

Two chickens can be seen pecking at colorful corn cobs placed on the grass. The home’s staircase and porch railings in the background provide a glimpse of the inviting entryway. Seasonal corn stalks and a potted mum add charm to the serene outdoor setting.

Home in East Haddam

5 out of 5 average rating, 25 reviews

Pet-Friendly Getaway in Historic East Haddam Home

Top guest favorite

The house features a modern black exterior with large windows that welcome natural light. A set of wooden steps lead to the main entrance, flanked by a deck that extends toward the surrounding landscape. A detached garage is visible in the background.

Home in East Hampton

5 out of 5 average rating, 22 reviews

CT River Retreat - Modern Home with CT River Views

The exterior of a charming two-story house is shown, featuring a spacious stone patio with seating areas. A large umbrella provides shade over a table set for outdoor dining. Lush greenery surrounds the home, complemented by large windows and a distinctive red front door.

Home in Clinton

5 out of 5 average rating, 13 reviews

Waterside retreat! 4BR/3BA with private dock/views

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