Best Vacation Homes in Thimble Islands
400 ft²
2 Guests
1 Bedroom
1 Bathroom
Ocean View
House
- Private Pool
- Oceanfront
- Hot Tub
CA $584/Night
For 7 Nights CA $4,089
301.39 ft²
6 Guests
4 Bedrooms
2 Bathrooms
House
- Private Beach
- Oceanfront
- Fireplace/Heating
CA $1,412/Night
For 7 Nights CA $9,883
1 Bedroom
1 Bathroom
Family Friendly
Bed & Breakfast
- Balcony/Terrace
- Breakfast
- Kitchen
CA $959/Night
For 7 Nights CA $6,712
1000 ft²
4 Guests
2 Bedrooms
1 Bathroom
Ocean View
Apartment
- Oceanfront
- Fireplace/Heating
- Ocean View
CA $374/Night
For 7 Nights CA $2,619
2002.09 ft²
8 Guests
3 Bedrooms
1 Bathroom
Ocean View
House
- Private Beach
- Oceanfront
- Ocean View
CA $627/Night
For 7 Nights CA $4,391
1300 ft²
4 Guests
2 Bedrooms
1 Bathroom
Ocean View
Apartment
- Oceanfront
- Fireplace/Heating
- Ocean View
CA $461/Night
For 7 Nights CA $3,226
5 Guests
1 Bedroom
1 Bathroom
Ocean View
Apartment
- Oceanfront
- Fireplace/Heating
- Ocean View
CA $362/Night
For 7 Nights CA $2,537
4 Guests
1 Bedroom
1 Bathroom
Ocean View
House
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
CA $1,328/Night
For 7 Nights CA $9,294
Thimble Islands Luxury Rentals
6500 ft²
22 Guests
11 Bedrooms
5 Bathrooms
Ocean View
House
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
CA $9,451/Night
For 7 Nights CA $66,159
8 Guests
4 Bedrooms
3 Bathrooms
Group Friendly
House
- Internet
- Child Friendly
- Laundry
CA $3,150/Night
For 7 Nights CA $22,053
3800 ft²
10 Guests
5 Bedrooms
4 Bathrooms
Ocean View
House
- Private Pool
- Hot Tub
- Fireplace/Heating
CA $2,337/Night
For 7 Nights CA $16,356
15 Guests
8 Bedrooms
4 Bathrooms
Ocean View
House
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
CA $1,693/Night
For 7 Nights CA $11,854
2100 ft²
6 Guests
3 Bedrooms
2 Bathrooms
Ocean View
House
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
CA $1,181/Night
For 7 Nights CA $8,271
2200 ft²
12 Guests
6 Bedrooms
2 Bathrooms
Ocean View
House
- Hot Tub
- Fireplace/Heating
- Ocean View
CA $973/Night
For 7 Nights CA $6,809
4 Guests
2 Bedrooms
1 Bathroom
Ocean View
Cottage
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
CA $873/Night
For 7 Nights CA $6,113
3000 ft²
10 Guests
5 Bedrooms
4 Bathrooms
Ocean View
House
- Oceanfront
- Fireplace/Heating
- Ocean View
CA $840/Night
For 7 Nights CA $5,878
Thimble Islands Pet Friendly Vacation Rentals
4 Guests
1 Bedroom
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
CA $311/Night
For 7 Nights CA $2,179
1 Bedroom
1 Bathroom
Ocean View
Apartment
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
CA $349/Night
For 7 Nights CA $2,445
4 Guests
2 Bedrooms
1 Bathroom
Ocean View
House
- Oceanfront
- Fireplace/Heating
- Ocean View
CA $429/Night
For 7 Nights CA $3,004
6 Guests
2 Bedrooms
1 Bathroom
Ocean View
Cottage
- Oceanfront
- Fireplace/Heating
- Ocean View
CA $563/Night
For 7 Nights CA $3,941
7 Guests
3 Bedrooms
3 Bathrooms
Family Friendly
House
- Private Pool
- Fireplace/Heating
- Pool
CA $498/Night
For 7 Nights CA $3,486
2800 ft²
6 Guests
3 Bedrooms
4 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
CA $557/Night
For 7 Nights CA $3,898
2000 ft²
9 Guests
4 Bedrooms
1 Bathroom
Ocean View
House
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
CA $1,631/Night
For 7 Nights CA $11,420
10 Guests
5 Bedrooms
4 Bathrooms
Ocean View
House
- Hot Tub
- Fireplace/Heating
- Ocean View
CA $3,008/Night
For 7 Nights CA $21,053
Thimble Islands Large Vacation Homes
14 Guests
6 Bedrooms
5 Bathrooms
Family Friendly
House
- Child Friendly
CA $1,260/Night
For 7 Nights CA $8,821
6 Guests
5 Bedrooms
3 Bathrooms
Family Friendly
House
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
CA $416/Night
For 7 Nights CA $2,915
3800 ft²
12 Guests
5 Bedrooms
4 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Breakfast
- Kitchen
CA $2,239/Night
For 7 Nights CA $15,675
1300 ft²
10 Guests
6 Bedrooms
3 Bathrooms
Ocean View
Cottage
- Hot Tub
- Spa
- Fireplace/Heating
CA $1,091/Night
For 7 Nights CA $7,635
8 Guests
5 Bedrooms
4 Bathrooms
Ocean View
House
- Oceanfront
- Fireplace/Heating
- Ocean View
CA $742/Night
For 7 Nights CA $5,197
2600 ft²
10 Guests
4 Bedrooms
5 Bathrooms
Ocean View
House
- Private Pool
- Oceanfront
- Pool
CA $415/Night
For 7 Nights CA $2,905
Why Choose Rent By Owner for your Thimble Islands Vacation Rental Homes?
What makes our Vacation Rentals special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Best Times to Visit Thimble Islands
When should you plan your Vacation Rentals stay?
Choosing the ideal time to visit ensures you can enjoy the tranquil beauty and outdoor activities that make this destination a perfect getaway, so consider your preferred season when exploring vacation rentals in the area.
Peak Season Highlights
Summer (June to August)
During the warmest months, you'll experience ideal weather for exploring the scenic waters and enjoying outdoor activities around the area.
Average Temperature Daytime: 75-85°F - Nighttime: 60-70°F
Fall (September to November)
This period offers crisp air and vibrant foliage, making it a perfect time to appreciate the natural beauty of this destination from your vacation rental.
Average Temperature Daytime: 65-75°F - Nighttime: 50-60°F
Off-Season Highlights
Winter (December to February)
The region sees fewer visitors, providing a quieter experience and cozy settings for relaxing in your vacation rental when the temperatures drop.
Average Temperature Daytime: 30-40°F - Nighttime: 20-30°F
Spring (March to May)
Early spring brings mild weather and blooming landscapes, offering a peaceful atmosphere before the busy summer season begins.
Average Temperature Daytime: 50-60°F - Nighttime: 40-50°F
Weekly Weather Forecast for Thimble Islands
How to Book Your Thimble Islands Vacation Rental Home
What's our booking process?
Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Explore and book the perfect rental in Thimble Islands
Common Vacation Rentals Amenities
What amenities can you expect?
Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Outdoor Amenities
- Enjoy outdoor dining areas perfect for savoring fresh sea breezes and scenic views.
- Take advantage of private docks or boat slips to explore the surrounding waterways by boat or kayak.
- Relax on spacious decks or patios that offer stunning vistas of the nearby islands and harbor.
- Utilize barbecue grills to host outdoor cookouts in the tranquil setting of the region.
- Make the most of lush, landscaped gardens or yard space ideal for outdoor activities and family gatherings.
- Have access to outdoor fire pits for cozy evenings with friends or loved ones under the stars.
- Explore nearby walking trails or nature paths that showcase the area's natural beauty and wildlife.
Top Attractions Around Thimble Islands
What attractions are nearby?
While here, you can enjoy exploring scenic boat tours, visiting charming local shops, and experiencing the tranquil natural beauty that surrounds this destination in Connecticut.
Family Activities
- Island Exploring Tours: Embark on guided boat tours around the Thimble Islands to discover its charming islets and learn about their unique histories, perfect for family adventures.
- Kayaking Adventures: Rent kayaks to paddle through the calm waters surrounding the region, offering a fun and interactive way for families to enjoy the scenic beauty here.
- Nature Walks and Wildlife Viewing: Take advantage of local trails and shoreline areas to observe native birds and marine life, making for engaging outdoor activities suitable for all ages.
- Seaside Picnics: Find picturesque spots along the water’s edge where your family can relax and share a meal, soaking in the peaceful surroundings of this charming destination.
Adult Activities
- Kayaking and Paddleboarding: Explore the calm waters surrounding the islands to enjoy a peaceful paddle in this scenic coastal region.
- Boat Tours and Cruises: Discover the area's hidden coves and charming islands through guided boat tours that highlight its maritime history and natural beauty.
- Sailing Experiences: Embark on a sailing adventure to soak in panoramic views of the coastline and appreciate the region's nautical heritage.
- Fishing Excursions: Engage in local fishing trips designed for adults seeking a relaxing day on the water with opportunities to catch local species.
Other Places to Stay in Thimble Islands, CT
Stony Creek - Thimble Islands Historic District
Thimble Islands Travel Tips
How Can You Make the Most of Your Stay?
- Plan Your Activities Ahead: Schedule your explorations and boat trips in advance to make the most of your time on this scenic destination.
- Choose a Waterfront Property: Opt for vacation rentals with water views to enjoy easy access to the area’s most picturesque spots and activities.
- Explore Local Dining Options: Take advantage of nearby eateries and waterfront cafes to experience the region’s fresh seafood and regional flavors.
- Respect the Natural Environment: Follow conservation guidelines to preserve the pristine beauty of the area during your stay and leave only footprints behind.
Transportation Options
- Ferry Services: You can enjoy scenic ferry rides to explore the Thimble Islands and its surrounding waters, offering a convenient way to access this charming destination.
- Renting a private boat provides flexible and intimate transportation around the area, allowing you to discover hidden spots at your own pace.
- Water taxis: Water taxis operate regularly, offering quick and reliable transit between the islands and the mainland for your convenience.
- Personal watercraft rentals: For a more adventurous approach, consider renting kayaks or paddleboards to navigate the tranquil waters connecting the islands here.
Local Customs Options
- Maritime Traditions: You will notice that the local customs here emphasize a deep respect for maritime history, reflected in community events and everyday life centered around boating and fishing.
- Local Seafood Cuisine: Savoring fresh seafood is an integral part of experiencing this destination’s culture, with many eateries serving dishes that celebrate the region’s maritime bounty.
- Community Festivals: Participating in or observing seasonal festivals and parades offers insight into the area’s close-knit community spirit and local traditions.
- Respect for Nature: Maintaining a harmonious relationship with the natural surroundings is a common custom, influencing both recreation and conservation efforts here.
Frequently Asked Questions About Thimble Islands?
1. What are the top vacation rentals in Thimble Islands?
There are a lot of options in Thimble Islands. If you plan on staying in the Thimble Islands area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Thimble Islands:
- Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub
- Unique, refined-rustic suite in Stony Creek village.
- Gorgeous Victorian direct ocean front single family six bedroom, ten rooms
- Stay Above Our Antique Shop In The Ridgeview Suite @ Stony Creek Depot
- The Queen of the Thimble Islands
- Waterfront home- Sleeps 10 - private beach-epic pool
- StedleyCreek! One bed-room apartment in the Stoney Creek area of Branford, CT.
- Your own Thimble Islands private cottage! (accessible by car via Old Quarry)
- MODERN GUESTHOUSE IN PRIVATE SETTING
- Beautiful Long Island Sound Direct Waterfront Cottage, private beach.
2. Which vacation homes in Thimble Islands are best for families?
If you are looking for a family-friendly vacation home in Thimble Islands, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Thimble Islands:
3. How many Rentbyowner vacation rentals are available in Thimble Islands?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 59 in the Thimble Islands area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Thimble Islands.
4. What is the cancellation policy for vacation rentals in the Thimble Islands area?
The cancellation policy varies by property. It is recommended to review the specific listing details or contact the property owner directly to understand the terms and any potential fees related to cancellations.
5. How do I ensure my reservation at a Thimble Islands vacation rental is secure?
Reservations are secured through verified listings with trusted hosts. Be sure to read the booking terms carefully and communicate directly with the property owner if you have any concerns before confirming your reservation.
6. Are there any additional fees or charges associated with staying in a vacation rental in this region?
Additional fees such as cleaning, service charges, or taxes may apply depending on the property. Details will be provided in the listing, so reviewing each property’s fee structure before booking is advisable.
7. What amenities can I expect from vacation rentals near the Thimble Islands?
Amenities vary by property but often include essentials like Wi-Fi, kitchen facilities, and parking. For specifics, consult the individual listing details or contact the host directly to confirm what is available during your stay.
8. How far in advance should I book my vacation rental in this destination?
It is recommended to book several months in advance, especially during peak seasons, to secure your preferred property. Availability details and suggested booking timelines are typically provided within each listing.
