Guesthouse vacation rentals in New Haven County

Find and book unique guesthouse rentals on Airbnb

Top-rated guesthouse rentals in New Haven County

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

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Guest favorite

Guesthouse in Southbury

4.94 out of 5 average rating, 309 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).

Superhost

Guesthouse in Milford

4.92 out of 5 average rating, 203 reviews

Chic Coastal Retreat: Modern Apt Steps from Beach

Enjoy our freshly renovated 2-bedroom apartment with a private entrance, kitchen, and in-unit washer/dryer all just a stone's throw from the beach. At Silver Sands State Park, take in views of Charles Island, accessible via a sandbar at low tide. Explore scenic bike trails or stroll the picturesque boardwalk. Perfect for families and group get togethers. Beach amenities are provided, including kayaks, and enjoy a private backyard where you can fire up the BBQ and fire pit. No pets, please.

Guest favorite

Guesthouse in Easton

4.84 out of 5 average rating, 101 reviews

Entire Guest House at Fox Pond Farm.

Recently renovated private guest house with access to swimming pool offers sleeping for eleven in four bedrooms. Tastefully decorated with all amenities. Close to Merritt Parkway and train to Manhattan. This is a natural refuge on eleven very private acres. Large private terrace faces westerly for amazing sunsets and offers a "Plein Air" environment for alfresco meals, cocktails and relaxation. An attached vegetable and flower garden with fountain offer a quiet space to relax and reflect.

Guest favorite

Guesthouse in Wallingford

5 out of 5 average rating, 98 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!

Guest favorite

Guesthouse in Milford

5 out of 5 average rating, 52 reviews

The studio downtown

The studio is a new, private, quiet, and peaceful space. It is situated on the second floor of a detached garage with a private entrance. It is located in the historic center of town, within walking distance of the train station, bars, restaurants, and beach. It is ideal for a couple looking for a beach town getaway. The studio has a king-size bed, an eating area, a kitchenette with a fridge, a sink, a double induction cooktop, a seating area, and a bathroom with a rain shower.

Guest favorite

Guesthouse in Portland

4.99 out of 5 average rating, 149 reviews

Guesthouse Farm Stay

Come stay with us on our working farm. Relax and take in our beautiful 12-acre property while sitting on the back deck, overlooking pastures. Or for a more interactive experience, join us on a farm tour during our morning and evening farm chores. Our farm was established in 1739 with a rich history in agriculture and livestock. Our cottage is studio-style with an open bedroom, living room, and dining area. There is a kitchette and bathroom with a shower for your convenience.

Guest favorite

Guesthouse in Berlin

4.9 out of 5 average rating, 29 reviews

Cozy, Spacious, Central Getaway

Spacious, cozy getaway. Near many popular events. Welcome to our comfy offering of a home away from home! Off street parking, prvt patio, view of parklike yard. Well lit pathways, arrows, outdoor cameras, alarm system for security/safety. Full kitchen and spacious bathroom. Dedicated workspace. Off rt 5/15 less than 5 minutes from I 84/I 91 festivals, colleges nearby. Dogs on premise but not in your area. Free Wi-Fi, and smart TV for video streaming.. PlS note no cable TV.

Guest favorite

Guesthouse in New Haven

5 out of 5 average rating, 7 reviews

East Rock Guest Cottage

New to Airbnb. Newly remodeled, light-filled, quiet, and comfortable 1-bedroom, two-story guest cottage located in the heart of New Haven's leafy, historic East Rock neighborhood. Queen bed upstairs and a Full-sized pull-out couch downstairs. Ideally located near East Rock Park and two blocks from coffee shops, neighborhood markets, and wine stores. Located in the host's backyard with a private entrance. 5 minutes from downtown New Haven. Ample street parking is available.

Guest favorite

Guesthouse in New Haven

4.94 out of 5 average rating, 282 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.

Guest favorite

Guesthouse in Guilford

4.99 out of 5 average rating, 479 reviews

Get Back to Nature at a Modern Wood Clad Getaway

FALL IS HERE. Crisp nights; gorgeous days. Hike on the trails.Stroll along the ocean. Ospreys; hawks; cardinals, blue jays, bluebirds, gold finches and more. Great places to shop and eat or just relax in our cozy guest house. Enjoy! We want you to have a relaxing stay with us, free from worry. We are located in a private area, away from public.

Guest favorite

Guesthouse in North Haven

5 out of 5 average rating, 70 reviews

The Stoli Cottage

Gay owned & Operated! Mike & JT (Hosts) Private Oasis, well maintained grounds! Located in a country setting! Go jogging or an evening walk in a beautiful park like setting across the street. There is the family dog that will love to be taken with you! Be our guest in a private family setting and relax!

Guest favorite

Guesthouse in Fairfield

4.96 out of 5 average rating, 187 reviews

Southport, CT across from BEACH

Located at Southport beach on Westport Line, this renovated 1 bedroom apartment totally private located above the garage and includes a full kitchen with new appliance and d/w and central air. Bdrm with queen, fine cotton sheets and towels, marble bath open living room w views.