House holiday rentals in Guilford

5 out of 5 average rating, 155 reviews

Home in North Haven

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!

4.89 out of 5 average rating, 242 reviews

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

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!

4.93 out of 5 average rating, 258 reviews

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

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.

4.98 out of 5 average rating, 194 reviews

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 East Shore

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.

4.99 out of 5 average rating, 335 reviews

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 Fair Haven

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.

4.94 out of 5 average rating, 124 reviews

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

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.

4.98 out of 5 average rating, 200 reviews

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

“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!

4.97 out of 5 average rating, 209 reviews

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

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.

4.99 out of 5 average rating, 112 reviews

A cottage nestled in a lush green setting is highlighted, surrounded by trees. The lawn is spacious and well-maintained, featuring a hammock between two trees. The structure showcases a simple facade with light blue siding, white window frames, and a chimney.

Home in Newtown

Comfortable home away from home- near everything

Price includes Airbnb fees. Cozy, pet-friendly cottage in a peaceful setting just 70 miles from NYC and minutes from I-84 (Exit 8 or 9). This clean & comfortable retreat features 3 bedrooms (2 queens, 1 full), and pull-out couch. Portable A/C's in summer, and fireplace for cozy nights. The greenhouse adds plenty of natural light, the yard is perfect for kids, the front deck is great for morning coffee, and the gas grill great for cooking out. High-speed WiFi and 3 smart TVs.

4.99 out of 5 average rating, 141 reviews

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.

Home in Haddam

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!

4.94 out of 5 average rating, 121 reviews

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

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

4.93 out of 5 average rating, 205 reviews

The exterior of a charming three-bedroom house is displayed, featuring a sloped roof and neatly trimmed bushes. A large tree provides shade in the front yard, while a stone pathway leads to the entrance. Side decorations include a swing and tree remnants.

Home in Bristol

Cozy Family Home - Kid & Pet Friendly

3 bedroom house on a quiet street. 5mins down the road from ESPN and Lake Compounce. Kid friendly. Pet friendly. Workspace available. 1 bedroom w/ king bed. 1 bedroom w/ queen bed. 1 bedroom w/ 2 twin beds. Fully finished basement with 60inch TV, kids toys and fitness equipment/stationary bike. Deck and below deck hang out space. Though we aren’t living here full time, it’s still the place we call home, and we will use it when it’s not booked. Long stays welcome.

Popular amenities for house rentals in Guilford

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

Superhost

A modern home is set on a spacious green lawn, featuring a combination of wood and metal siding. Large windows allow natural light to fill the interior. A stone pathway leads to the entrance, framed by lush landscaping and trees, enhancing the outdoor tranquility.

Home in The Hamptons

4.89 out of 5 average rating, 116 reviews

Modern East Hampton Home w/ Heated Saltwater Pool

4.89 out of 5 average rating, 104 reviews

Home in The Hamptons

Serene + chic, nestled in nature, near attractions

4.83 out of 5 average rating, 107 reviews

A serene view of the Long Island Sound is captured at sunset, featuring soft pastel hues in the sky. A few clouds are present, and the gentle water surface reflects the vibrant colors. A flagpole with an American flag stands prominently in the foreground.

Home in Milford

Spacious 4 bedroom, oasis with ocean views galore

4.92 out of 5 average rating, 160 reviews

A swimming pool with clear blue water is surrounded by a spacious deck. Lounge chairs with striped cushions are arranged for relaxation. Colorful umbrellas provide shade over outdoor sofas, and lush greenery in the background enhances the serene environment.

Home in The Hamptons

Large heated pool, games room, near private beach

4.9 out of 5 average rating, 119 reviews

A swim spa with dual zones is shown, featuring illuminated blue and red lights. The adjacent outdoor area includes a large screen displaying a sports event. Steam rises from the hot tub, creating a relaxing ambiance in the evening setting.

Home in Hamden

Sleeping Giant Stay/Swim Spa w/Tread/Tonal/Peleton

4.96 out of 5 average rating, 170 reviews

The game room features vibrant lighting and a chalkboard wall that displays 'Casino Stay & Play House.' A foosball table is positioned alongside arcade machines, with several stools lined up against a bar counter. The floor is finished in light wood, enhancing the dynamic atmosphere.

Home in Montville

Casino Stay & Play House w/Hot Tub, Game Room

4.93 out of 5 average rating, 197 reviews

A cozy living room features exposed wooden beams and warm wood-paneled walls. A stone fireplace is centrally located, with a basket of wood beside it. A rug with rich colors lays under a wooden table, surrounded by comfortable seating, inviting a relaxed atmosphere.

Home in Litchfield

Stunning Views, Bucolic Bliss in 1790s Farmhouse

4.97 out of 5 average rating, 152 reviews

An expansive aerial view reveals a private pool surrounded by lush green grass and trees. A small pond is visible nearby, with vibrant foliage framing the scene. Open fields stretch into the distance, highlighting the rural setting on the property.

Home in Windham

mid century ranch style house on farmland

Weekly house rentals

A view of the exterior of the blue house, showcasing a white lattice railing along the patio. Steps lead down to the water, with a calm blue surface reflecting the sky. Potted plants add a touch of greenery to the space.

5 out of 5 average rating, 36 reviews

Charming 2BR Beach House, Overlooking the Water

4.9 out of 5 average rating, 31 reviews

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

Boulder Lake House Retreat

4.87 out of 5 average rating, 23 reviews

A single-story blue home is presented, featuring a combination of large windows and a welcoming front entry. Stone steps lead to the door, with landscaped rocks and greenery enhancing the outdoor space.

Home in East Haven

Private Entire Home • Close to New Haven & Shore

A spacious living area is presented, featuring a light-colored sectional sofa paired with a round coffee table. A dining table with six chairs occupies one corner. Large windows allow natural light to fill the room, with light curtains softly framing the views outside.

5 out of 5 average rating, 59 reviews

Coastal Farmhouse walking distance to town

A bright kitchen space is highlighted by pale blue cabinetry and rich wooden countertops. A wooden table with chairs sits at the center, adorned with a vase of flowers. Large windows allow natural light to illuminate the area, enhancing its inviting feel.

4.73 out of 5 average rating, 150 reviews

Purple Button Factory Sleeps 6 Walk to Town Green

4.84 out of 5 average rating, 80 reviews

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 Short Beach

Beautiful 3 bedroom shoreline house

A modern home is showcased with a stone foundation and large windows, allowing natural light to fill the space. A spacious deck is visible, featuring colorful seating options and a stone wall that surrounds a well-maintained lawn, complemented by leafy trees.

5 out of 5 average rating, 24 reviews

Coast and Country Private Estate

4.89 out of 5 average rating, 9 reviews

An open living area features exposed wooden beams and a brick fireplace, contributing to an inviting ambiance. A plush green sectional sofa is arranged around a round wooden coffee table, with natural light flooding the space through the large windows.

Home in North Haven

North Acre: Oversized Ranch near Yale & New Haven

Private house rentals

4.91 out of 5 average rating, 33 reviews

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

The Gait House at High Gait Farm

Superhost

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.

4.97 out of 5 average rating, 37 reviews

Edwin Leete House

4.9 out of 5 average rating, 39 reviews

The exterior of a modern cottage is presented with a black wood facade and multiple windows. A front porch is seen, partially enclosed with slatted wood. Lush green grass and shrubbery frame the entrance, creating a welcoming approach to the home.

Home in North Fork

Waterfront NoFo Cottage w/ public beach access

4.93 out of 5 average rating, 96 reviews

The living room features a modern design with a curved green and orange sofa surrounding a light wood coffee table. A striking black fireplace provides a focal point against a light wall. A statue and decorative elements contribute to the welcoming ambience.

Home in West Haven

Westshore Luxury

5 out of 5 average rating, 9 reviews

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 Star Branford Cozy Cottage

4.95 out of 5 average rating, 40 reviews

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.

Home in Haddam

The Farmhouse Stay

5 out of 5 average rating, 25 reviews

The estate is set on expansive green lawns, framed by mature trees. The picturesque house features a charming combination of traditional architecture and modern details, with expansive verandas and a large outdoor deck providing ample space for relaxation.

Home in East Haddam

Elegant Countryside Estate