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Guesthouse vacation rentals in Fairfield County

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Top-rated guesthouse rentals in Fairfield County

Guests agree: these guesthouse rentals are highly rated for location, cleanliness, and more.

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Top guest favorite

A modern living space features a comfortable sofa, a circular coffee table, and a television unit. Large sliding glass doors create a seamless view of the outdoors, with natural greenery visible beyond the private deck. Soft natural light fills the room, enhancing its inviting ambiance.

Guesthouse in Guilford

4.99 out of 5 average rating, 498 reviews

Get Back to Nature at a Modern Wood Clad Getaway

SPRING IS HERE--Glorious spring birds. Come and enjoy a wonderful time in our guest house--warm days, cool nights. You can Hike on the trails, and Stroll along the ocean. Ospreys; hawks; cardinals, blue jays, bluebirds, gold finches and more are here year round. Great places to shop and eat or catch a show at one of New Haven’s renowned museums or broadway theatres or relax. Enjoy! We want you to have a relaxing stay with us, free from worry. We are located in a private area, away from public.

A covered outdoor seating area features a combination of woven chairs and a sofa arranged around a stone floor. Soft lighting is provided by string lights overhead, while rustic wooden beams and walls create a warm, inviting backdrop.

Guesthouse in Southbury

4.93 out of 5 average rating, 328 reviews

Charming Guest Cottage with Modern Amenities

Private Guest House set on 5+ Acres, along with Historic Colonial Home. Bright and sunny and over looks pool and gardens (seasonal). Efficiency with Kitchen featuring 2 burner stove, Microwave, Under Counter Fridge/Freezer/Ice Maker, Dishwasher, Granite Counters. . Dining Area, Great Room w/ soaring ceilings, French Doors to private patio, hardwood floors. Loft with full-sized bed, and sofa can be a to Queen Size Sleeper. Full bath with extra-large shower. Dog friendly (approval needed).

Top guest favorite

An outdoor seating area is set among trees, featuring stone pathways and a gravel surface. A circular fire pit is surrounded by seating, and a small dining set with two chairs is positioned nearby. A grassy space adds greenery to the tranquil setting.

Guesthouse in Mahopac

4.95 out of 5 average rating, 238 reviews

Lakeview Guesthouse with Sauna

Art and light filled spacious studio with panoramic views overlooking lake Mahopac perched on a steep hill. A short 5 min walk down the hill to swimming/paddleboarding/canoeing. Walkable to an on-the-lake restaurant/ dining/ takeout options + boba tea! Drivable to farm fresh food markets, restaurants and art museums. Cedar dry Sauna on property for use. Nearby towns and hikes include Fahenstock Park, Pound Ridge, Cold Spring, Beacon, Ridgefield, or walk up the hill to trails of Volz park!

A charming cottage exterior is surrounded by lush greenery and autumn foliage. The two-story structure features a balcony adorned with potted plants. Large windows create a welcoming appearance, while the grassy area in front offers a peaceful outdoor setting.

Guesthouse in Wilton

4.97 out of 5 average rating, 124 reviews

The Cozy Little Cottage

Charming guest cottage on our property on 1.5 acres in pastoral neighborhood, 7 minutes to Wilton center and 8 to Westport center. The cottage is separate from the main house, connected by a breezeway, above the garage. It is quaint and cozy. High end kitchen appliances include gas range, mini fridge, microwave and mini dishwasher. The bedroom has a queen bed and the living room has a futon couch which folds down. It’s perfect for 1-2 adults, can comfortably fit 3 people if one is a child.

A dark wooden barn is surrounded by lush greenery, showcasing a set of stairs leading to the second floor. A paved patio area features a table and chairs, inviting outdoor relaxation among the tranquil natural setting.

Guesthouse in Brewster

4.94 out of 5 average rating, 145 reviews

Sherwood Barn - close to ski mountain

Our guests stay on the SECOND floor of the barn in a 1200 Sq Ft, fully reno'd apt that sleeps 6. Located about 1 hour from NYC you will find peace and serenity in the middle of nature on this 4 acre estate (that also contains our main home) where you can get away from it all. unwind this way or visit local attractions like Thunder Ridge Ski Mountain, snowshoe/ X Country skiing, hike/bike/running trails, restaurants and local cafe's. Great oasis to kick back and spend time with family.

Top guest favorite

A private deck features comfortable seating arrangements with soft cushions. A decorative area rug is placed beneath a small table. String lights hang overhead, enhancing the cozy ambiance of the outdoor space. The red exterior of the loft adds charm to the setting.

Guesthouse in Wallingford

5 out of 5 average rating, 121 reviews

The Garden Loft - A Charming Choate Stay

Welcome to The Garden Loft! Located in the heart of downtown Wallingford, CT. This traditional and historic New England carriage house has been completely renovated in the summer of 2022 into a peaceful, cozy, bright & airy loft. We are a 3 minute walk from downtown where you will find a variety of restaurants, bars, a brewery & only 1 mile from from Choate Rosemary Hall. A 15 minute drive to Yale University & downtown New Haven. Get ready to relax, get cozy & enjoy The Garden Loft!

Top guest favorite

A tranquil gravel road lined with lush green trees stretches into the distance. Natural stone borders are visible along the edge of the pathway, providing a rustic charm. Soft light filters through the leaves, creating a serene and inviting ambiance.

Guesthouse in Cold Spring

4.99 out of 5 average rating, 168 reviews

Modern+bright forest escape - near village & train

Modern, efficient, and elegant private flexible garden apt. Guesthouse can be used as a studio apartment, or as a private personal retreat space for art/work/rest/meditation. Hiking trails available right out the door, and just a few minutes walk to Cold Spring's vibrant Main Street and Metro North train station to NYC and beyond. Comfortable bed, all modern amenities. Private patio. Native pollinator gardens and forest surround. Solar orientation brings in natural light.

A colorful storefront features large windows displaying a variety of items, including clothing and gifts. The exterior is painted in vibrant hues, while hanging flower baskets add a touch of charm. A lamppost stands in front, enhancing the inviting atmosphere.

Guesthouse in Hastings-on-Hudson

4.92 out of 5 average rating, 852 reviews

★Tiny House Cottage 35 min to NYC on Hudson River★

Please read the entire listing to set expectations. Super charming, slightly quirky, private Shangri-La with backyard chickens in the artistic and quaint Rivertowns, 35 minutes from NYC along the Hudson River. The Tiny House escape is reminiscent of sleepaway camp (rustic), yet tastefully curated with eclectic art and furnishings. Sleeping loft nest with 8-step ladder or pull-out sofa bed. Fenced-in yard. FREE 24/7 street parking. Read on…

A narrow hallway features a stacked washer and dryer set against one wall, providing convenience for guests. Wood flooring extends throughout the space, with a view of a dining area in the background illuminated by natural light. A doorway leads outdoors, enhancing accessibility.

Guesthouse in New Haven

4.93 out of 5 average rating, 310 reviews

Square 6ix

Inviting, eclectic, and completely private, this single family stand-alone guest house is an intimate and engaging haven. Stylishly decorated with mid-century modern furniture and adorned with pieces from local artists, this quiet home has a separate entrance, separate porch, high ceilings, and a fully equipped kitchen. The guest house is located a walking-block away from the charms of Westville Village and Edgewood Park.

The nighttime image showcases the illuminated marquee of the Paramount Theater, featuring vibrant lights and signage. A crowd gathers outside, with classic cars parked along the street. The architecture of the theater is highlighted against the dark sky, enhancing its vintage charm.

Guesthouse in Peekskill

4.92 out of 5 average rating, 277 reviews

Peekskill Carriage House Downtown Studio

Located close to the center of town, this is the perfect launchpad to experience local restaurants, coffee houses, the Paramount Theater, shopping, etc. and a short drive to stunning hikes, the Hudson Valley and beyond. The apartment is ideal for one or two and features a kitchenette, bathroom, dining island, comfortable queen bed, and couch. peekskillcarriagehouse.com

Top guest favorite

A serene pool area is framed by neatly manicured grass and surrounding trees. Comfortable seating is placed around the pool, with views of the lake and expansive sky in the background. A white fence adds a touch of charm to the peaceful setting.

Guesthouse in Brewster

4.99 out of 5 average rating, 321 reviews

The Cottage by the Lake: Hudson Valley Indulgence

The Cottage by the Lake is a cozy, secret get-away on the scenic banks of the Croton Watershed. About an hour from NYC, it’s on the property of an 1850 farmhouse & has a fully equipped kitchen & bath, cathedral ceiling, working fireplace & cozy sleeping loft. The patio has a fire pit and gas bbq. It’s the ideal place for those seeking to work from home.

A charming guest studio features a triangular roofline and a welcoming porch. Two wooden chairs are positioned on the porch, facing double glass doors that open into the interior. The surrounding area is filled with trees, creating a natural and serene atmosphere.

Guesthouse in Bedford

4.92 out of 5 average rating, 209 reviews

Private Guest Studio

Just 39 miles north of Manhattan. Relax and unwind, to enjoy endless opportunity for outdoor activities, fine dining, antiquing, or just loving the peace & quiet of this private studio, in a manicured setting, with wood burning stove, porch, heated pool (June-August), and private footpaths leading to an open field.

Vacation rentals for every style

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Cabins

Kick off your hiking boots at these rustic lodgings

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Convenient locations with everyday essentials

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Luxurious estates for the ultimate escape

Popular amenities for Fairfield County guesthouse rentals

Free parking on premises

Air conditioning

Family-friendly guest house rentals

A gravel pathway leads to a dark wooden fence, framing the entrance to the property. Lush greenery and trees surround the area, while a spacious lawn extends towards a cottage and rolling hills in the background, under a partly cloudy sky.

Guesthouse in Gaylordsville

4.96 out of 5 average rating, 111 reviews

Adorable Cottage in Pastoral Setting

A spacious living area features a large sectional sofa adorned with decorative pillows, complementing a dining area with a round table and four chairs. Bright overhead lights illuminate the space, which includes a modern kitchen visible in the background.

Guesthouse in Milford

4.92 out of 5 average rating, 206 reviews

Chic Coastal Retreat: Modern Apt Steps from Beach

A serene view captures the landscaped yard leading to a tidal inlet, framed by lush green grass. The calm waters reflect the blue sky and nearby trees, with residential homes visible in the background. A small dock extends into the inlet from the opposite bank.

Guesthouse in Norwalk

5 out of 5 average rating, 71 reviews

Cottage by the Sea

The space features a decorative chandelier that provides warm lighting. Skylights allow natural light to illuminate the room, while a row of decorative items is visible on the shelf above. Sheer curtains offer a soft texture against the walls.

Private room in New Haven

4.82 out of 5 average rating, 210 reviews

Amadeus "English Garden Studio"

A charming cottage exterior is framed by lush greenery, featuring large front glass doors and a sloped roof. Potted flowers adorn the entrance, while a shaded sitting area with comfortable chairs is visible beside the pathway, inviting relaxation in a serene setting.

Guesthouse in Stormville

4.97 out of 5 average rating, 175 reviews

Hudson Valley Cottage with Pond Access

The exterior of the Equestrian Suite is showcased, featuring a two-story structure with a blend of brick and wood. A wrap-around balcony offers scenic views, and lush greenery surrounds the property, complementing the tranquil mountain setting.

Guesthouse in Beacon

4.94 out of 5 average rating, 400 reviews

Cozy Mountainside Suite - Minutes from Beacon

The exterior of the two-story cottage is framed by lush greenery, featuring a welcoming porch with white columns. Large windows allow natural light to flood the interior. The gentle slope of the roof and classic shutters enhance the charming architecture, while a hint of red barn peeks in the background.

Guesthouse in Norwalk

5 out of 5 average rating, 23 reviews

Guest Cottage in Rowayton

A two-story house with a light-colored exterior is framed by neatly trimmed hedges and a lush green lawn. The front porch features white railings and steps leading to the entrance, while large windows with white trim allow natural light to enter.

Guesthouse in Yonkers

4.76 out of 5 average rating, 124 reviews

St James Guest House

Guest house rentals with a patio

Top guest favorite

A bright sleeping area features a spacious bed with light bedding, positioned beneath a vaulted ceiling. Floor-to-ceiling windows provide views of the woods, while a small desk and chair are set against one wall for workspace. A television is mounted for entertainment.

Guesthouse in Greenwich

4.95 out of 5 average rating, 96 reviews

The Cottage in Greenwich

A rustic exterior of a large studio is framed by trees showcasing fall colors. The structure features a unique design with a gabled roof and wooden paneling. A gravel driveway and a stone patio are visible, providing access to the entrance amid a serene natural setting.

Guesthouse in Southbury

4.93 out of 5 average rating, 71 reviews

The Nest. Large studio in the Woods.

A bright living area is framed by large windows showcasing a wooded view. A dark green sofa with white pillows is positioned alongside two light-colored armchairs. A wooden coffee table rests on a patterned area rug, with a dining table visible in the background.

Guesthouse in Pound Ridge

5 out of 5 average rating, 16 reviews

Renovated guesthouse on private 7 acre property

Top guest favorite

The exterior of the guest house is framed by manicured gardens, featuring two decorative statues positioned beside a pea gravel walkway. A small patio area includes a round table with two chairs, creating a serene spot for outdoor relaxation.

Guesthouse in Waccabuc

4.99 out of 5 average rating, 96 reviews

French Guest House in Waccabuc

Top guest favorite

A modern kitchen features white cabinetry and stainless steel appliances, highlighted by a central island with bar seating. A skylight allows natural light to illuminate the space, while patterned rugs add a touch of texture to the floor. Decorative shelving displays various items on the wall.

Guesthouse in Guilford

4.95 out of 5 average rating, 101 reviews

Guilford Lakes Cottage, with hot tub and fire pit.

Top guest favorite

A modern kitchen features a central island with a sleek cooking range and ventilation hood. Bright windows provide views of Norwalk Harbor and the surrounding landscape. Light cabinetry complements the stainless steel appliances, creating a clean and airy space for meal preparation.

Guesthouse in Norwalk

5 out of 5 average rating, 22 reviews

Waterfront Getaway - Norwalk, CT

Top guest favorite

A serene saltwater pool is surrounded by well-maintained grass and lush greenery. Natural stone pavers outline the pool area, providing a harmonious blend with the surrounding landscape. Several lounge chairs are positioned nearby for relaxation, enhancing the outdoor atmosphere.

Guesthouse in Bedford Hills

5 out of 5 average rating, 49 reviews

The Perch, a luxe cottage with pool 1h from NYC

The cottage is surrounded by lush greenery, featuring a charming entrance with a white door and a stone chimney. A greenhouse sits alongside, filled with plants. The front yard is lined with vibrant shrubs and framed by blooming trees under a clear blue sky.

Guesthouse in Wilton

4.98 out of 5 average rating, 46 reviews

The Ciderhouse Cottage - private escape in Wilton

Guest house rentals with a washer and dryer

An outdoor space is furnished with multiple white chairs surrounding a central fire pit. A large umbrella stands next to the seating area. Sunlight highlights the wooden decking, with plant life subtly framing the scene, contributing to a fresh and airy environment.

Guesthouse in Mamaroneck

4.9 out of 5 average rating, 164 reviews

Your Modern Guest Wing Near NYC

Top guest favorite

A well-maintained garden features lush green grass and a variety of trees and flowering plants, creating a vibrant natural setting. The surrounding property presents a charming two-story building, partially obscured by foliage, against a clear blue sky, enhancing the tranquil ambiance.

Guesthouse in Larchmont

4.98 out of 5 average rating, 46 reviews

Beautiful guesthouse - Larchmont

An outdoor fire pit is surrounded by wooden adirondack chairs, offering a cozy space for gathering. The sun sets in the background, casting a warm glow over the lush tree line. A stone border surrounds the fire pit, providing a natural aesthetic.

Guesthouse in Easton

4.85 out of 5 average rating, 104 reviews

Entire Guest House at Fox Pond Farm.

A scenic view of a calm waterway is framed by a wooden deck. Two white chairs with blue stripes are positioned for relaxation. A small table holds decorative items, while a dock extends into the water, surrounded by greenery and gentle waves.

Guesthouse in Fairfield

4.95 out of 5 average rating, 22 reviews

The Creekside Cottage

Top guest favorite

A clean kitchen countertop is displayed with a tray holding decorative hand soap and dish soap. A roll of paper towels is presented on a holder, with a piece creatively folded into a bow shape. The backsplash features light blue tiles, enhancing the modern aesthetic.

Guesthouse in Bethel

5 out of 5 average rating, 20 reviews

Tranquil getaway cottage in charming neighborhood

Top guest favorite

The image depicts the exterior of a modern, dark-colored guest house surrounded by greenery. A well-maintained stone pathway leads to the entrance, with decorative rock features in the foreground. Potted plants add subtle color, enhancing the tranquil outdoor setting.

Guesthouse in Litchfield

5 out of 5 average rating, 55 reviews

Guesthouse at Bantam Woods - 2 bedrooms

The cottage is nestled among lush trees, highlighted by a distinctive stone chimney. Expansive glass doors reflect the surrounding greenery, inviting natural light inside. The structure is surrounded by verdant shrubs, creating a harmonious connection with nature.

Guesthouse in Pound Ridge

4.93 out of 5 average rating, 75 reviews

A Lovely Cottage in the Woods with Private Pool

Guesthouse in Watertown

4.9 out of 5 average rating, 42 reviews

Private studio guesthouse

Destinations to explore