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Guesthouse vacation rentals in Fairfield

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Top-rated guesthouse rentals in Fairfield

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Top guest favorite

A charming cottage features wood shingle siding and a neatly arranged entrance. The front yard showcases a manicured area with green grass, accompanied by a duck and a chicken. Nearby, expansive fields and a rustic barn complete the serene rural landscape.

Guesthouse in Portland

4.98 out of 5 average rating, 246 reviews

Guesthouse Farm Stay

Come stay with us on our historic working farm! Relax on the back deck and enjoy views of our 12-acre property and peaceful pastures. For a more hands-on experience, join us for a tour to get a closer look at life on the farm. Established in 1739, our farm has a rich history in agriculture and livestock. The cozy studio-style cottage features an open living space with combined bedroom, living, and dining area, along with a kitchenette and bathroom with a shower for your comfort and convenience.

A white Dutch door is framed by rustic wooden walls, showcasing a combination of horizontal and vertical planks. A small lantern hangs nearby, and a woven basket adorns the wall beside the door. A simple bench with a patterned cushion sits on the side.

Guesthouse in Southbury

4.93 out of 5 average rating, 349 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

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

4.95 out of 5 average rating, 402 reviews

Cozy Mountainside Suite - Minutes from Beacon

The Equestrian Suite at Lambs Hill is a private estate with panoramic views overlooking the Hudson River & downtown Beacon. This beautifully-designed luxury suite sits atop a barn home to Icelandic horses & miniature donkeys, & features an outdoor hot tub, red light therapy, gourmet kitchen, & wrap-around decks. 1 mile to Beacon's Main St, 2 miles to Metro North train station & DIA: Beacon. We can host a max of 2 guests & have some dangerous features for kids so guests should be adults only.

Top guest favorite

A modest wooden house features large glass doors that lead to a spacious deck. The surrounding green lawn is complemented by well-kept shrubs and trees. Sunlight casts a warm glow on the exterior, highlighting the structure's simple charm.

Guesthouse in Norwalk

4.99 out of 5 average rating, 151 reviews

1BR full cottage, 1 min walk to private beach

Enjoy time at this lovely studio located in the heart of Rowayton, a charming New England seaside village bounded on one side by Long Island sound and the other by a tidal inlet. Based in the southwest corner of CT, we are just a 1 minute walk to 2 separate and secluded beaches as well as 2 private, well manicured parks. Great amenities in town including tennis, sailing, outdoor yoga, sunbathing, plus nice restaurants. Pedestrian and dog friendly town; you don't even need a car while here.

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

4.96 out of 5 average rating, 134 reviews

The Cozy Little Cottage

Charming guest apartment on our property on 1.5 acres in pastoral neighborhood, 7 minutes to Wilton center and 8 to Westport center. The cottage is a good size for 1-2 adults, can fit 3 people if one is a child. The unit is separate from our 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. We have a twin air mattress for use in the living room.

A rustic black barn is showcased, featuring wooden doors and exterior lighting. A paved driveway leads up to the entrance, bordered by a well-maintained lawn and trees. The surrounding natural landscape enhances the barn's secluded charm.

Guesthouse in Brewster

4.94 out of 5 average rating, 156 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

The exterior of a bright red carriage house is surrounded by lush gardens filled with various flowers and greenery. Two large windows and a white door are visible, adding charm to the traditional New England design. A well-maintained lawn complements the vibrant landscape.

Guesthouse in Wallingford

5 out of 5 average rating, 131 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

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, 111 reviews

French Guest House in Waccabuc

A mini Versailles just outside of NYC - located on a private and gated eight acre estate with its own lake in Waccabuc, NY. Surrounded by 18C statuary, manicured gardens and fountains, it’s equivalent to staying in a 5-Star European luxury hotel suite (house designed by David Easton) with its heated stone floors and heated towel rack, luxury linens, gold taps and serene private entrance. (.7mi from Waccabuc Country Club, 60 min from NYC by car or train - Katonah train St)

A cozy living area features mid-century modern furniture, including an orange armchair and a sleek glass coffee table. A gallery wall displays various artworks, complemented by natural light from two windows. A small dining area with a round table and four chairs contributes to the inviting layout.

Guesthouse in New Haven

4.93 out of 5 average rating, 323 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.

Top guest favorite

The interior features large windows allowing natural light to illuminate the space. A spiral staircase leads to the loft. A cozy seating area includes a white sofa and a decorative fireplace. Lake views are visible through the glass doors, enhancing the serene atmosphere.

Guesthouse in Brewster

4.99 out of 5 average rating, 323 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 is set among trees, featuring large glass doors that open to a stone patio. Four white adirondack chairs surround a fire pit, providing a relaxed outdoor gathering space. The studio's design reflects a serene and inviting atmosphere in nature.

Guesthouse in Bedford

4.92 out of 5 average rating, 218 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.

A light-filled sitting area features large windows showcasing views of the river and surrounding hills. Two black armchairs and a round table with two chairs are positioned on a polished wooden floor, creating a serene space for relaxation.

Guesthouse in Hyde Park

4.99 out of 5 average rating, 745 reviews

Modern cottage with Hudson River view

Relax and enjoy your stay in a bright, modern cottage with windows overlooking the river and a wraparound deck. Whether you are looking to relax along the river, explore Hyde Park historic properties or discover the incredible natural beauty of the Hudson Valley, this cottage is an ideal escape.

Vacation rentals for every style

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A space thats all yours, with room for everyone

Popular amenities for Fairfield guesthouse rentals

Free parking on premises

Air conditioning

Family-friendly guest house rentals

Top guest favorite

Two swans crafted from towels are positioned at the center of a spacious bed, forming a heart shape. Surrounding the swans is a decorative arrangement of rose petals in shades of red. The bed's textured spread complements the soft green pillows in the background.

Guesthouse in Nesconset

5 out of 5 average rating, 26 reviews

Private charming Studio Cottage in Nesconset

A spacious living area features a plush sectional sofa adorned with decorative pillows. A rectangular coffee table sits in the center, accompanied by a small potted plant. Natural light enters through a window, while a private entrance door is visible in the background.

Guesthouse in Southington

4.94 out of 5 average rating, 16 reviews

Cozy Private Guest Suite

Guesthouse in Southbury

4.94 out of 5 average rating, 78 reviews

The Nest. Large studio in the Woods.

Top guest favorite

A cozy bungalow exterior is framed by lush greenery, with a wooden deck featuring two outdoor chairs. The entrance is marked by a white door and an array of windows, inviting natural light into the space.

Guesthouse in Carmel Hamlet

4.9 out of 5 average rating, 87 reviews

Sweet lil' house among the boulders LONG TERM STAY

Top guest favorite

A private cabin is nestled among lush greenery, showcasing a large deck with two Adirondack chairs positioned for relaxation. The cabin features large glass doors that open to the natural surroundings, enhancing the peaceful atmosphere.

Guesthouse in Kingston

4.99 out of 5 average rating, 146 reviews

Chic, Private Cabin with Stunning River Views

Top guest favorite

A spacious living area is presented with a large flat-screen TV mounted on a white entertainment unit. A soft gray sofa sits nearby, and a decorative area rug enhances the room's aesthetic. Natural light streams in through a front door adorned with a glass panel.

Guesthouse in Watertown

4.93 out of 5 average rating, 73 reviews

Private studio guesthouse

A charming cottage is nestled among lush greenery, featuring a light-colored exterior with multiple windows. The inviting entrance is framed by neatly trimmed shrubs, while a stone pathway leads to the front door. A spacious yard with trees adds to the serene setting.

Guesthouse in Greenwich

4.88 out of 5 average rating, 42 reviews

Beautiful Cottage in Greenwich CT

Top guest favorite

A cozy living room features a large flat-screen TV mounted on the wall, accompanied by a sleek entertainment unit. A comfortable couch is draped with a soft blanket, and an armchair is positioned nearby. Natural light enters through two windows, brightening the neutral decor.

Guesthouse in Mamaroneck

4.97 out of 5 average rating, 65 reviews

Spacious guest suite near water

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, 100 reviews

The Cottage in Greenwich

Top guest favorite

A cozy sitting room features exposed wooden beams and a brick fireplace. Two comfortable leather chairs are arranged around a wooden coffee table. Natural light enters through multiple windows adorned with sheer curtains, illuminating the space, which is enhanced by decorative touches like artwork and plants.

Guesthouse in Philipstown

4.99 out of 5 average rating, 108 reviews

Historic 1 bedroom home in Cold Spring, NY

Top guest favorite

A lush green field extends towards the horizon, framed by clusters of trees. The sky is filled with varying shades of clouds, reflecting a soft light from the setting sun. The peaceful rural landscape evokes a sense of tranquility.

Guesthouse in Gardiner

4.99 out of 5 average rating, 180 reviews

Red Barn Retreat - Shawangunk Mountains Getaway

A serene outdoor space features comfortable seating arrangements overlooking a flowing brook, framed by lush greenery. A fire pit and a rustic outdoor heater add charm, while the sound of the nearby waterfall enhances the tranquil environment.

Guesthouse in Sharon

4.94 out of 5 average rating, 125 reviews

Cottage with a Waterfall View

A spacious hot tub is situated on the deck, surrounded by a wooden fence for privacy. Two chairs and a small table are positioned nearby, while additional seating options are visible in the background. The setting is framed by trees, offering a natural ambiance.

Guesthouse in Guilford

4.95 out of 5 average rating, 109 reviews

Guilford Lakes Cottage, with hot tub and fire pit.

An open living space is illuminated by natural light from multiple windows, featuring a cozy sofa, wooden coffee table, and a dining area with metal chairs. A spiral staircase leads to a loft space, while a door opens to a private outdoor deck.

Guesthouse in Accord

4.9 out of 5 average rating, 137 reviews

Tiny Horse Barn

Top guest favorite

A comfortable sleeping area features a spacious bed with a blue quilt and decorative pillows. Two side tables with lamps are placed beside the bed. A small arrangement of flowers adds a touch of color. Blinds cover the window, allowing for adjustable natural light.

Guesthouse in Shirley

4.96 out of 5 average rating, 104 reviews

La casita J place

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, 27 reviews

Waterfront Getaway - Norwalk, CT

Guest house rentals with a washer and dryer

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, 212 reviews

Chic Coastal Retreat: Modern Apt Steps from Beach

A spacious bedroom features a large bed with neutral bedding, complemented by a comfortable, modern seating area. Natural light fills the room through multiple windows, and built-in shelves showcase books and decorative items, adding functionality and style to the space.

Guesthouse in Mamaroneck

4.9 out of 5 average rating, 166 reviews

Your Modern Guest Wing Near NYC

The exterior of the guest house features a stone facade complemented by a sloped roof. Lush greenery surrounds the property, and the driveway is lined with gravel. Two white planters with flowers are positioned in front of the entrance, while the sky displays a mix of clouds and blue.

Guesthouse in Easton

4.85 out of 5 average rating, 108 reviews

Entire Guest House at Fox Pond Farm.

A bright living and dining area features a navy blue sofa adorned with decorative pillows. A wooden dining table set for four occupies one side, while a light rug anchors the space. Sunlight filters through sheer curtains, enhancing the room's inviting ambiance.

Guesthouse in Huntington Station

4.97 out of 5 average rating, 105 reviews

Modern fully updated 2nd Floor apartment

A charming cottage is depicted, featuring a dark exterior with bright pink doors. Two pink chairs and a small table are positioned outside on a gravel area, surrounded by potted plants. Trees frame the backdrop, contributing to a serene setting.

Guesthouse in Dover Plains

4.87 out of 5 average rating, 125 reviews

Spilt Milk Cottage - Hudson Valley, NY

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

4.94 out of 5 average rating, 96 reviews

A Lovely Cottage in the Woods

Top guest favorite

A modern studio features a spacious bed draped in white bedding with blue accents, alongside a cozy seating area with a dark sofa. Floor-to-ceiling glass windows provide stunning views of the river and open onto a private terrace, enhancing the serene ambiance.

Guesthouse in Ulster Park

4.99 out of 5 average rating, 431 reviews

Escape to a Sleek, Serene Studio on the Riverbank

A combined living and dining area features a dark wood dining table with white chairs and a vase of flowers. A comfortable sofa sits alongside a light armchair, with a standing lamp providing soft illumination. Natural light filters through a nearby window.

Guesthouse in Glastonbury

4.82 out of 5 average rating, 105 reviews

The Hospitable Homestead-Kid Friendly & Pets too!

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