Guesthouse vacation rentals in Long Island Sound
Find and book unique guesthouse rentals on Airbnb
Top-rated guesthouse rentals in Long Island Sound
Guests agree: these guesthouse rentals are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Long Island Sound guesthouse rentals
Family-friendly guest house rentals
Guesthouse in East Meadow
4.95 out of 5 average rating, 138 reviewsPetite Cottage
Jan 31 – Feb 7
Guesthouse in South Salem
4.93 out of 5 average rating, 220 reviews1795 colonial w private 2 bd rm, 1 bth,LR,Kit apt
Apr 6 – 13
Guesthouse in Charlestown
4.88 out of 5 average rating, 269 reviewsCozy All Season Cabin Near Beach at Rockbriar Farm
Feb 9 – 16
Guesthouse in Shelter Island
4.97 out of 5 average rating, 105 reviewsWaterfront carriage house studio
Aug 20 – 27
Guesthouse in Jamesport
4.97 out of 5 average rating, 107 reviewsWalk to Beautiful Beach in Heart of Wine Country
Mar 26 – Apr 2
Guesthouse in Ulster Park
4.85 out of 5 average rating, 457 reviewsHudson Valley Hideaway
Nov 15 – 22
Guesthouse in Groton
4.94 out of 5 average rating, 385 reviewsQuiet studio with sleeping loft and deck
Aug 13 – 20
Guesthouse in New Paltz
4.99 out of 5 average rating, 387 reviewsRidge View Walk-Up | Your GUNKS Home
Jun 11 – 18
Guest house rentals with a patio
Guesthouse in Montgomery
4.93 out of 5 average rating, 121 reviewsLuxury mins from angry orchard and city winery
Dec 3 – 10
Guesthouse in Gardiner
4.99 out of 5 average rating, 137 reviewsRed Barn Retreat - Shawangunk Mountains Getaway
Jun 12 – 19
Guesthouse in Sharon
5.0 out of 5 average rating, 65 reviewsCottage with a Waterfall View
Aug 21 – 28
Guesthouse in Shirley
4.97 out of 5 average rating, 35 reviewsLa casita J place
Dec 9 – 16
Guesthouse in North Castle
4.98 out of 5 average rating, 44 reviewsMagical 1700's 1 bedroom cottage
Jul 31 – Aug 7
Guesthouse in Southbury
4.96 out of 5 average rating, 52 reviewsThe Nest. Large studio in the Woods.
Feb 27 – Mar 6
Guesthouse in Kerhonkson
4.95 out of 5 average rating, 55 reviewsCozy Catskills Cottage
Sep 10 – 17
Guesthouse in Newtown
5.0 out of 5 average rating, 45 reviewsFarm Cottage
Sep 16 – 23
Guest house rentals with a washer and dryer
Guesthouse in New Haven
4.94 out of 5 average rating, 241 reviewsSquare 6ix
Aug 31 – Sep 7
Guesthouse in Brewster
5.0 out of 5 average rating, 290 reviewsThe Cottage by the Lake: Hudson Valley Indulgence
Aug 1 – 8
Guesthouse in Stonington
4.97 out of 5 average rating, 223 reviewsTrue Artist Loft, 5 minutes to downtown Mystic
Oct 25 – Nov 1
Guesthouse in Stonington
4.99 out of 5 average rating, 188 reviewsSuper Adorable Cottage + Fire pit + King Bed!
Dec 8 – 15
Guesthouse in Bedford Hills
4.91 out of 5 average rating, 112 reviewsBarrett's Sanctuary
May 22 – 29
Guesthouse in Mamaroneck
4.94 out of 5 average rating, 127 reviewsYour Modern Guest Wing Near NYC
Aug 11 – 18
Guesthouse in Stanfordville
4.92 out of 5 average rating, 164 reviewsEco Cottage in the Woods
Feb 14 – 21
Guesthouse in Warwick
4.96 out of 5 average rating, 251 reviewsBellvale Guest House on Solar Powered Mini-estate
Dec 8 – 15
Destinations to explore
- House rentals New York
- Guesthouse rentals New York
- Guesthouse rentals United States
- House rentals United States
- Guesthouse rentals Manhattan
- House rentals Manhattan
- House rentals Brooklyn
- Guesthouse rentals Brooklyn
- Fitness-friendly rentals Long Island Sound
- Tiny house rentals Long Island Sound
- Villa rentals Long Island Sound
- Rentals with a hot tub Long Island Sound
- Boutique hotel rentals Long Island Sound
- Rentals with lake access Long Island Sound
- Rentals with outdoor seating Long Island Sound
- Rentals with a washer and dryer Long Island Sound
- Loft rentals Long Island Sound
- Rentals with beach access Long Island Sound
- Smoking-friendly rentals Long Island Sound
- Beachfront rentals Long Island Sound
- Hotel rentals Long Island Sound
- Apartment rentals Long Island Sound
- Farmstay rentals Long Island Sound
- Rentals with a fireplace Long Island Sound
- Pet-friendly rentals Long Island Sound
- Townhouse rentals Long Island Sound
- Family-friendly rentals Long Island Sound
- Rentals with breakfast Long Island Sound
- Cottage rentals Long Island Sound
- Rentals with an EV charger Long Island Sound
- Rentals with a kayak Long Island Sound
- Bungalow rentals Long Island Sound
- Rentals with a fire pit Long Island Sound
- Kid-friendly rentals Long Island Sound
- Monthly Rentals Long Island Sound
- Bed and breakfasts Long Island Sound
- Condo rentals Long Island Sound
- Private suite rentals Long Island Sound
- House rentals Long Island Sound
- Rentals with pools Long Island Sound
- Rentals with a patio Long Island Sound
- Luxury rentals Long Island Sound
- Waterfront rentals Long Island Sound
- Rentals with a home theater Long Island Sound
- Rentals with a sauna Long Island Sound
- Wheelchair accessible rentals Long Island Sound
- Rentals with an accessible height toilet Long Island Sound
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom