
House vacation rentals in Thimble Islands
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Top-rated house rentals in Thimble Islands
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Hamptons Oceanfront Oasis
Escape the hustle & bustle of city life and unwind at this stunning home in the Hamptons. The oceanfront oasis is the perfect way to wake up to ocean views, beaches and nearby restaurants. Relax on our spacious deck - perfect for morning coffees & sunset cocktails. It is just a short drive to the train station & only 15 minutes from the airport for quick getaways. For your safety, the home is equipped with Ring cameras and one-use key codes. Book now and experience the ultimate Hamptons escape!

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.

Amazing Home close to Everything -
Elegantly designed home featuring modern appliances, a seasonal heated pool, and situated just moments away from ocean beaches, Wolffer Vineyard, and the vibrant Bridgehampton/Sag Harbor villages. Set within meticulously curated landscaping, this property embodies perfection and meticulous attention to detail. Familiarize yourself with our disclosures, guidelines, and house rules. We maintain a strict no events, no parties, and no smoking policy — our home and property grouds are smoke-free.

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.

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.

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
Popular amenities for Thimble Islands house rentals
House rentals with a pool

Stylish+Cozy Hamptons Winter Getaway-5min to Beach

Lux 4BR Private Indoor Heated Pool - Mystic Home

Spacious 4 bedroom, oasis with ocean views galore

Stunning luxury Retreat I Wineries & Fall Farm Fun

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

Peaceful Light-Filled Guesthouse 1 Hour From NYC

Exclusive Sag Harbor Compound

Casino Stay & Play House
Weekly house rentals

The Gait House at High Gait Farm

Westshore Luxury

Charming 2BR Beach House, Overlooking the Water

Private Entire Home • Close to New Haven & Shore

Coastal Farmhouse walking distance to town

Marina Chic: Bright Seaside Gem

Guilford Beach Cottage

The Eagle- Private Beach
Private house rentals

Beachside Bliss w/ Game Room, Gym & Golf Green

Cozy beach cottage close to everthing

"Sunset Shores" Lakeside Oasis

Chic East Hampton 7 Bedroom, 7 Bath, heated Pool

Stylish Modern Home, 4-Bedroom, Madison CT

Whispering Meadow House

3BD w/ Hot Tub Close 2 New Haven+ Yale | FREE EV

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