
House holiday rentals in Thimble Islands
Find and book unique houses on Airbnb
Top-rated house rentals in Thimble Islands
Guests agree: These houses are highly rated for location, cleanliness and more.

Beachfront Paradise
Beautiful beachfront home available weekly in season third week of June through Labor Day) and nightly (2 night min.) off season. Step out the door and into the sand. Sit on the porch and watch sailboat races from Niantic Bay Yacht Club just steps away. Close to downtown Niantic with restaurants, shops, etc. 18 miles from Mohegan Sun Casino. Attractions within 1/2 hour: Beautiful Mystic, CT, several vineyards, Harkness State Park, Eugene O'Neill Theatre, U.S. Coast Guard Academy, golf courses.
4.97 out of 5 average rating, 227 reviews
Spacious 5 BR Home near town
Spacious 5 Bedroom 2 story farmhouse in quiet neighborhood of Historic Guilford. Perfect for family gatherings, reunions, special occasions, traveling work crews, or a simple vacation getaway. There is ample room for everyone to relax and unwind. The kitchen is stocked with enough dinnerware and appliances for all Just 1 mile from town, the home offers easy access to I-95, New Haven, Yale Univ. and the scenic Connecticut shoreline. Hiking trails & local PYO Farm Market are a short walk away.
4.83 out of 5 average rating, 126 reviews
Gorgeous 3BR | Private Beach Access | Weekly Stays
Enjoy our newly remodeled 3 bedroom home with water views and a 250 foot walk to Limewood Beach with private beach access. Our home is a 5 minute walk to 5 restaurants and bars, and a 5 minute Uber ride to the train station. Enjoy swimming and boating in the warmer months, or take a stroll along the beach and collect shells and sea glass all year round. No matter which time of year you visit, you will appreciate the tranquility of the ocean and will feel completely relaxed during your stay.
4.87 out of 5 average rating, 215 reviews
WaterviewsTakeWedding pics,CollegeTours Yale&Beach
PETS ALLOWED! Spectacular unobstructed Long Island Sound views year-round, out your front door along Pardee Seawall! This exceptional shore line property offers all new furniture & amenities. Minutes to wedding venues-perfect for getting dressed on your wedding day & taking photos literally right outside your door (props available). Near: Tweed NH Airport, beach, Yale University & Hosp, restaurants & museums. All new furniture, linens/towels, grill, fire pit, centralAC, WIFI. Onsite parking.
4.98 out of 5 average rating, 238 reviews
Romantic Getaway at The Lake!
Beautiful year round getaway! Relax and have a glass of wine by the lake. Wake early to enjoy the sun rising directly over the lake with a fresh cup of coffee. Enjoy direct lake access on a trophy bass lake including a beautiful dock. Hot tub overlooking the water open year round. Enjoy dinner in front of beautiful gas fireplace. Amazing sunrises and colorful sunsets. The location and amenities make for a fantastic romantic getaway for two! Centrally located 30 minutes from the Mohegan Casino.
4.93 out of 5 average rating, 361 reviews
Modern farmhouse w/ pool, beach, horses and winery
A new, modernized farmhouse with a heated saltwater pool in the heart of North Fork. Nestled on an acre of lush, fully fenced yard, the home can easily accommodate up to 8 guests and all pets! Minutes away from Love Lane (Mattituck's charming downtown), Breakwater Beach (one of best beaches in North Fork), Mattituck train station and surrounding the award winning Bridge Lane Vineyards and picturesque Seabrook Horse Farm, this bucolic home offers the perfect setting for a North Fork getaway.
4.93 out of 5 average rating, 138 reviews
Designer Beach Retreat on Exclusive Cedar Beach
Welcome to your own slice of heaven! Enjoy dinner in your Chef's kitchen while watching one of the most radiant sunsets you will ever see. Stunning views from the private rear deck or snuggled on the couch inside the living room. Wade into Long Island Sound with semi-private beach access 250 feet away. The property is 5 doors down from the CT Audubon Society, known for its epic views and wildlife watching. The sunrises & sunsets are beautiful! 15 minutes to Yale. We can't wait to host you!
4.97 out of 5 average rating, 270 reviews
The Lighthouse: Beach Cottage Getaway by the Sea!
Relax at this unique and tranquil getaway. Long Island Sound to the left, hiking trails to the right. Come kick your feet up at this quiet dead-end road. Enjoy all the modern amenities in this gem of a cottage community. Restaurants and nightlife are just a quick stroll away. Avoid roadside hotels and take a vacation for a night, week, or longer! Check in anytime and at your convenience!No keys to lose or to return! This property provides secure, keyless entry with an August Smart Lock!
4.98 out of 5 average rating, 259 reviews
Steps to Beach • Hot Tub • Game Room • Water Views
Beautiful coastal beach house directly across from a private beach and tennis club with complimentary guest access. Backing up to a serene marsh with stunning views, this home offers a peaceful, upscale setting perfect for families and groups. Relax in the hot tub with outdoor TV, fire pit, and kayaks. Inside features 4 bedrooms, a workspace, and a new game room with a 100” TV, pool table, shuffleboard, and darts. Minutes from Branford’s town center, dining, and waterfront attractions.
4.99 out of 5 average rating, 113 reviews
Waterside Beach Retreat
Beautiful New England period home steps from the beach on the Long Island Sound. Recently renovated from top to bottom with new kitchen and bathrooms, hardwood floors throughout. Idyllic location on quaint & quiet street. Hide away and relax or discover the many local attractions - water sports, fishing, winery, antique stores, scenic walks, premium outlet shopping are all on your doorstep. Ideally located off the I-95 halfway between NYC & Boston, both of which are a train ride away.
4.96 out of 5 average rating, 227 reviews
Purple Button Factory Sleeps 8, Walk to Town Green
Close to CT shoreline. 4 bdrm, 2 bath, 2,200 sq ft home on dead-end street, across from Meadow River, tidal marsh. Great bird-watching! Mid-week specials. Walk to Guilford Town Green, restaurants, shopping. Fully-equipped kitchen. Wood-burning fireplace. Clean, airy, peaceful space. Eclectic art & beach-comber decor. Large back yard with fire pit. Deck for functions, family gatherings, relaxing. Historic property was once a button factory! Original chestnut, wide-board floors.
4.75 out of 5 average rating, 167 reviews
Westshore Luxury
Relax in the cozy living spaces, unwind in the bonus room, or take a peaceful stroll along the sandy beach just steps from your door. Enjoy breathtaking sunrises and sunsets over the water, fall asleep to the soothing sound of waves, or explore the scenic shoreline by bike. Whether you’re visiting for a quiet weekend escape or a longer stay, this charming beach home offers the perfect balance of comfort and tranquility. Quiet home for rest and relaxation — no parties or events.
4.82 out of 5 average rating, 186 reviewsPopular amenities for Thimble Islands house rentals
House rentals with a pool

Stunning Hamptons Waterfront Escape w/ Sunset View
4.87 out of 5 average rating, 144 reviews
Serene East Hampton Escape - Warm Pool til Nov
4.99 out of 5 average rating, 156 reviews
Sleeping Giant Stay/Swim Spa w/Tread/Tonal/Peleton
4.88 out of 5 average rating, 130 reviews
Luxury modern farmhouse with heated pool & hot tub
4.93 out of 5 average rating, 148 reviews
Southampton Village Newly Built Gem
4.97 out of 5 average rating, 103 reviews
Casino Wine Down House w/Pool, Game Room, Big Deck
4.92 out of 5 average rating, 333 reviews
Southamp Waterview, DogsFREE! Kayaks, Ping-Pong
4.95 out of 5 average rating, 206 reviews
Breathtaking home with unforgettable views & pool!
4.92 out of 5 average rating, 134 reviewsWeekly house rentals

Beach Sanctuary on the Long Island Sound
4.94 out of 5 average rating, 62 reviews
Picturesque Waterfront Villa
4.9 out of 5 average rating, 21 reviews
Breathtaking Panoramic Waterfront
4.93 out of 5 average rating, 46 reviews
5* Branford Cottage with access to Owenego Club.
4.94 out of 5 average rating, 47 reviews
3BR Waterfront Oasis on Joshua Cove, Private Beach
5.0 out of 5 average rating, 47 reviews
Guilford shoreline private home
5.0 out of 5 average rating, 4 reviews
The Connecticut Cottage | Historic Modern Charm
4.97 out of 5 average rating, 31 reviews
The Eagle- Private Beach
4.97 out of 5 average rating, 65 reviewsPrivate house rentals

Entire home - Cheerful 4 bedroom on the shoreline.
5.0 out of 5 average rating, 40 reviews
Cozy beach cottage close to everthing
4.9 out of 5 average rating, 60 reviews
Private Entire Home • Close to New Haven & Shore
4.95 out of 5 average rating, 77 reviews
Bungalow by the Bay
5.0 out of 5 average rating, 3 reviews
The Gait House at High Gait Farm
4.94 out of 5 average rating, 49 reviews
Quarry House: Mid-Century Modern
5.0 out of 5 average rating, 25 reviews
Mulberry Seaside Cottage
5.0 out of 5 average rating, 40 reviews
Scenic Mulberry Point Connecticut Beach House
4.94 out of 5 average rating, 85 reviewsDestinations to explore
- Yale University
- Mohegan Sun
- Foxwoods Resort Casino
- Cooper's Beach, Southampton
- Fairfield Beach
- Thunder Ridge Ski Area
- Ocean Beach Park
- Mystic Seaport Museum
- Mystic Aquarium
- Southampton Beach
- University of Connecticut
- Sunken Meadow State Park
- Soundview Beach
- Hammonasset Beach State Park
- Powder Ridge Mountain Park & Resort
- Compo Beach
- Wölffer Estate Vineyard
- Ocean Beach
- Sleeping Giant State Park
- Sherwood Island State Park
- Ski Sundown
- Meschutt Beach
- Orient Beach State Park
- Ditch Plains Beach





