Guesthouse vacation rentals in Connecticut

Find and book unique guesthouse rentals on Airbnb

Top-rated guesthouses in Connecticut

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

Guest favourite
Guesthouse in Stonington
True Artist Loft, 5 minutes to downtown Mystic
The Dacha, as it has lovingly been called for almost 80 years was built in 1945 originally as a studio for the artist that resided on the property. The unique structure is truly one of a kind, fully insulated for winter and tucked away from the road, sitting on a quiet piece of land, just 5 minutes to downtown Mystic. Enjoy modern comforts and a designers decor, while settling in front of the fire, or taking a short drive to all that Mystic has to offer- hiking, water, shops and restaurants.
Aug. 11 – 18
$402 CAD per night
4.98 out of 5 average rating, 214 reviews
Guest favourite
Guesthouse in Southbury
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).
Mar. 31 – Apr. 7
$246 CAD per night
4.93 out of 5 average rating, 264 reviews
Guest favourite
Guesthouse in Norwalk
Adorable one-bedroom guesthouse with parking
Private, peaceful, cozy renovated cottage next to my house in a quiet residential neighborhood. Originally used as a painting and design studio, ideal for short stays and as a workspace. Luxury queen bed in upstairs loft; downstairs with refrigerator/freezer, Keurig with coffee and tea; microwave; Wifi, heat, air conditioning. There is NO RUNNING WATER in the cottage, but a lovely PRIVATE FULL BATH is just steps away in the main house AVAILABLE 24/7 exclusively for you during your stay.
May 18 – 25
$167 CAD per night
4.99 out of 5 average rating, 202 reviews

Popular amenities for Connecticut guesthouses

Family-friendly guesthouses

Guest favourite
Guesthouse in Groton
Quiet studio with sleeping loft and deck
Mar. 24 – 31
$185 CAD per night
4.94 out of 5 average rating, 379 reviews
Guest favourite
Guesthouse in Fairfield
Southport, CT across from BEACH
Apr. 27 – May 4
$406 CAD per night
4.96 out of 5 average rating, 169 reviews
Guest favourite
Guesthouse in New Milford
Charming Cottage w/Pastoral Views
Jan. 4 – 11
$270 CAD per night
4.94 out of 5 average rating, 176 reviews
Guest favourite
Guesthouse in New London
Fully Renovated, Ocean Views, Fireplace & Beach
Nov. 3 – 10
$486 CAD per night
4.98 out of 5 average rating, 97 reviews
Superhost
Guesthouse in Glastonbury
59 Old Maids Lane pool house
Jan. 9 – 16
$213 CAD per night
4.71 out of 5 average rating, 58 reviews
Guest favourite
Guesthouse in Mystic
Maxson House - a serene and stylish getaway
Sep. 4 – 11
$534 CAD per night
4.78 out of 5 average rating, 90 reviews
Guest favourite
Guesthouse in Sprague
House on Little River / Writer Retreat
Jun. 17 – 24
$221 CAD per night
4.97 out of 5 average rating, 187 reviews
Guest favourite
Guesthouse in Milford
Silversands Air-Bnb You’re right Here!
Aug. 28 – Sep. 4
$411 CAD per night
4.92 out of 5 average rating, 191 reviews
Guesthouse in North Stonington
Ashwillett Gardens Studio
Jun. 27 – Jul. 4
$138 CAD per night
4.87 out of 5 average rating, 529 reviews
Guesthouse in Winchester
Year-round Lakefront Highland Lake - Immaculate
Apr. 29 – May 6
$418 CAD per night
4.97 out of 5 average rating, 59 reviews
Guest favourite
Guesthouse in Barkhamsted
Farmington River Carriage House Pleasant Valley CT
Aug. 29 – Sep. 5
$366 CAD per night
4.87 out of 5 average rating, 86 reviews
Guest favourite
Guesthouse in Norwalk
Cottage by the Sea
Nov. 23 – 30
$365 CAD per night
5.0 out of 5 average rating, 57 reviews

Guesthouses with a patio

Guest favourite
Guesthouse in Sharon
Cottage with a Waterfall View
Mar. 19 – 26
$164 CAD per night
5.0 out of 5 average rating, 55 reviews
Guest favourite
Guesthouse in New Milford
Luxury in the Litchfield Hills
Dec. 10 – 17
$321 CAD per night
5.0 out of 5 average rating, 39 reviews
Guest favourite
Guesthouse in Southbury
The Nest. Large studio in the Woods.
Feb. 5 – 12
$246 CAD per night
4.96 out of 5 average rating, 51 reviews
Guest favourite
Guesthouse in Guilford
Guilford Lakes Cottage, with hot tub and fire pit.
Jun. 2 – 9
$466 CAD per night
4.99 out of 5 average rating, 75 reviews
Guest favourite
Guesthouse in Greenwich
The Cottage in Greenwich
Jan. 25 – Feb. 1
$320 CAD per night
4.94 out of 5 average rating, 62 reviews
Guest favourite
Guesthouse in Newtown
Farm Cottage
Oct. 27 – Nov. 3
$403 CAD per night
5.0 out of 5 average rating, 42 reviews
Guest favourite
Guesthouse in Washington
Private, cozy woodland getaway.
May 10 – 17
$332 CAD per night
5.0 out of 5 average rating, 15 reviews
Guest favourite
Guesthouse in Guilford
Page Guest House
Jan. 13 – 20
$341 CAD per night
5.0 out of 5 average rating, 56 reviews
Guest favourite
Guesthouse in Wilton
The Ciderhouse Cottage - private escape in Wilton
Jul. 28 – Aug. 4
$525 CAD per night
5.0 out of 5 average rating, 20 reviews
Guest favourite
Guesthouse in Madison
The Rising Tide Cottage
Sep. 7 – 14
$412 CAD per night
4.95 out of 5 average rating, 56 reviews
Guest favourite
Guesthouse in East Hampton
Family-Friendly Lakeside Cottage
Sep. 27 – Oct. 4
$316 CAD per night
4.86 out of 5 average rating, 14 reviews
Guest favourite
Guesthouse in Madison
Beachy & Bright Carriage House/5 min walk to Beach
Feb. 12 – 19
$631 CAD per night
4.97 out of 5 average rating, 64 reviews

Guesthouse rentals with a washer and dryer

Guest favourite
Guesthouse in Glastonbury
Unique luxurious private building in historic area
Aug. 8 – 15
$323 CAD per night
4.96 out of 5 average rating, 131 reviews
Guest favourite
Guesthouse in Stonington
Super Adorable Cottage + Fire pit + King Bed!
Jul. 8 – 15
$380 CAD per night
4.99 out of 5 average rating, 181 reviews
Guest favourite
Guesthouse in New Hartford
Litchfields West Hill New Hartford Four Season BNB
Apr. 19 – 26
$201 CAD per night
4.88 out of 5 average rating, 72 reviews
Guest favourite
Guesthouse in Madison
The Barn by the Sound
May 8 – 15
$310 CAD per night
5.0 out of 5 average rating, 57 reviews
Guest favourite
Guesthouse in Mystic
HERON HOUSE MYSTIC, CT.
Sep. 8 – 15
$477 CAD per night
5.0 out of 5 average rating, 90 reviews
Guest favourite
Guesthouse in Old Lyme
Studio Four-Entire Guesthouse near CT River
Sep. 1 – 8
$402 CAD per night
5.0 out of 5 average rating, 40 reviews
Guest favourite
Guesthouse in Litchfield
Cozy remodeled Cottage
Nov. 11 – 18
$360 CAD per night
4.89 out of 5 average rating, 9 reviews
Guest favourite
Guesthouse in Stonington
Merry Hall Farmhouse
Apr. 9 – 16
$463 CAD per night
4.97 out of 5 average rating, 59 reviews
Guest favourite
Guesthouse in Essex
Adorable 2 bedroom guesthouse in Essex village
Jan. 17 – 24
$533 CAD per night
5.0 out of 5 average rating, 25 reviews
Guest favourite
Guesthouse in East Haven
Adorable private 1-bedroom guesthouse with parking
Jul. 21 – 28
$432 CAD per night
4.94 out of 5 average rating, 31 reviews
Guest favourite
Guesthouse in Weston
Weston Guest Cottage with Tennis/Pickleball Court
Aug. 10 – 17
$445 CAD per night
5.0 out of 5 average rating, 34 reviews
Superhost
Guesthouse in Fairfield
Fairfield Town/Beach "Story-Book" Cottage w/Pool
Mar. 31 – Apr. 7
$499 CAD per night
4.67 out of 5 average rating, 3 reviews

Destinations to explore