
House vacation rentals in Thimble Islands
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Top-rated house rentals in Thimble Islands
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Luxury Stay in Expansive Historical Home
The Bassett House, originally built in 1802, this large historic farmhouse was elegantly remolded in 2018. North Haven, CT is centrally located and just minutes from Yale, Quinnipiac, UNH, and SCSU as well as shopping, the best restaurants, hiking trails state parks and beaches, and many local attractions including various vineyards. If you’re planning a business trip or a gathering for family or friends, then our home can provide you with an exceptional level of comfort during your time in CT!

Beach Cottage by the Sea
Beautiful 1920's beach cottage with beach access just across the street. Enjoy the sea breeze, ocean views, and sound of the waves lapping in this quaint home with unique architecture. Ten minutes to downtown New Haven and Yale for great places to eat, museums, and nightlife. Public beach and playground nearby. Warm and welcoming community. Master bedroom has vaulted ceilings and deck with views of the sea. Central Air, Cable TV, outdoor grill, plenty of parking. Enjoy this lovely home!

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.

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.

3 bed home (2 King, 1 Queen bed) 4MINS FROM BEACH!
Enjoy this 3 beds, 2 bath home 4 mins from the beach! There is a beautiful stone fireplace in the living room to enjoy on a cold fall/winter night. You can relax and enjoy a book on one of our cozy lounge chairs on the sun porch. There is also a deck on the side of the house to enjoy the fresh air. Located only 15 mins from historic downtown New Haven, voted best pizza in the country! 8 mins from wedding venues, Amarante’s Seacliff and Anthony’s Oceanview. 8 mins from Tweed-New Haven Airport.

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!

New Lake Front Home w/ Game Room & Stunning Views
Relax and enjoy the breathtaking views of this new contemporary lake front home. Offering the best of New England, 7 min. from Foxwoods, 15 min. from Mohegan Sun, with multiple choices of hiking, boating, shopping and dining. Stunning 14' cathedral ceilings, fully equipped kitchen w/ granite counter tops, tiled shower w/ full amenities and a full game room. You can not get any closer to the water! This 1 Bdrm, w/ open low ceiling loft, sleeps 6, 1100 square ft. building completed in 2022.

“The Lighthouse” A Beach Cottage 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!

*Sale* HGTV reno! Steps to shops & water | Firepit
*Inquire now monthly discount Jan* *Brand New Major Renovation in 2023* • Fully renovated, designer beach house • Steps away from quaint downtown •1 block from water •Walk to beach, restaurants, coffee, ice cream, deli & convenience store, liquor and more... • Luxe, white, 100% cotton sheets & fluffy duvets •FULLY FENCED backyard with outdoor seating, BBQ grill, & fire pit .Easy drive to Sacred Heart, Fairfield, & Yale .STEPS to Tyde wedding venue .Fiber internet for fast speeds

Cozy Comforts!
Keep it simple at this peaceful and centrally-located place. Completely open concept and fully renovated. Country living yet just minutes to downtown Middletown and Wesleyan University. Come stay at our home away from home! We are about 20-25 min from the shoreline or travel in the other direction and you’ll be in our state’s capital, Hartford. We are only about 10-15 min from Wesleyan and downtown Middletown for shopping and great restaurants! You don’t want to miss this one!

Charming home, easy access to everything Branford
Full home, comfortable and very well equipped. Private fenced in backyard with patio dining area. Off-street (driveway) parking. Short Walk to the Shoreline Greenway trail. Less than a mile to downtown, parks, beaches, restaurants, marina, Stoney Creek Brewery. Near event venues, The Owenego and Pine Orchard club. Close to New Haven. Family(kid) Friendly home with private fenced in backyard with patio dining area. Equipped with Pack N Play, highchair, booster seat, etc

Oceanfront Retreat: Modern Beach House
Escape to this luxurious 4-bedroom, 2.5-bath oceanfront home on the stunning Long Island Sound. Enjoy direct beach access, a private hot tub, and a fully equipped patio with a gas grill and dining area. Perfect for families or groups, this retreat offers breathtaking views, a full kitchen, arcade games, and modern amenities. Located minutes from restaurants and shops, it’s ideal for relaxation or adventure. Book now for a perfect blend of comfort and coastal charm.
Popular amenities for Thimble Islands house rentals
House rentals with a pool

Stylish+Modern Cape w/Saltwater Pool-5min to Beach

4BR Private Indoor Heated Pool - Lux Mystic Home

Spacious 4 bedroom, oasis with ocean views galore

Classic Southampton Village Home w/ Pool

Stunning luxury Retreat I Wineries & Fall Farm Fun

GOOD VIBEZ HOUSE! Mini Golf-Pool-Hot Tub-GameRoom!

Exclusive Sag Harbor Compound

Sleeping Giant Stay/Swim Spa w/Tread/Tonal/Peleton
Weekly house rentals

The Gait House at High Gait Farm

Beach House in Private Community on LI Sound

Westshore Luxury

Quarry House: Mid-Century Modern

Coastal Farmhouse walking distance to town

Whispering Meadow House

3BD w/ Hot Tub Close 2 Beach+Free EV charge

Marina Chic: Bright Seaside Gem
Private house rentals

Edwin Leete House

Cozy beach cottage close to everthing

Beachside Bliss w/ Game Room, Gym & Golf Green

Beach Cottage | Steps to Water| Fireplace|Firepit

The Jewel of The Cove - Historic Coastal Retreat

Chic East Hampton 7 Bedroom, 7 Bath, heated Pool

Stylish Modern Home, 4-Bedroom, Madison CT

The Farmhouse Stay
Destinations to explore
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- Yale University
- Foxwoods Resort Casino
- Fairfield Beach
- Southampton Beach
- Cooper's Beach, Southampton
- Ocean Beach Park
- Walnut Public Beach
- Thunder Ridge Ski Area
- Shinnecock Hills Golf Club
- Rowayton Community Beach
- Napeague Beach
- Cedar Beach
- Groton Long Point Main Beach
- TPC River Highlands
- Brownstone Adventure Sports Park
- Woodmont Beach
- Silver Sands Beach
- Sunken Meadow State Park
- Sandy Beach
- Jennings Beach
- Wildemere Beach
- Mystic Seaport Museum
- Outer Beach at Smith Point County Park
- Seaside Beach