Thimble Islands holiday rentals

We found 360 holiday rentals — enter your dates for availability

Holiday rentals with weekly discounts – Thimble Islands

Showing deals for:8 Jan - 15 Jan

Living area
Interior
Living area
Living area
Excellent
(5 reviews)

Luxury New Haven Retreat • Private Pool, Gym, Cinema • Near Yale & Beaches

East Haven

7% off
AU$4,638
for 7 nights, 1 home
AU$663 per night
includes taxes & fees
Luxury New Haven Retreat • Private Pool, Gym, Cinema • Near Yale & Beaches
Private kitchen
Back deck
Living room, bathed in morning light
Interior
Wonderful
(90 reviews)

Historic New England home ,Reunions Beach pass

Guilford

7% off
AU$3,583
for 7 nights, 1 home
AU$512 per night
includes taxes & fees
Historic New England home ,Reunions Beach pass
master bedroom, king bed.
Interior
Home from the water. (Blue house in center of photo)
(new photo 6/25/2011)
Exceptional
(54 reviews)

Beautiful Waterfront Beach House for Family Vacations

Branford

8% off
AU$8,743
for 7 nights, 1 home
AU$1,249 per night
includes taxes & fees
Beautiful Waterfront Beach House for Family Vacations
Living Room
Lake View
Living Room
The Kitchen
Exceptional
(16 reviews)

Gorgeous Waterfront 3 Bedroom, 1.5 Bathroom Unit.

New Haven

8% off
AU$2,243
for 7 nights, 1 home
AU$320 per night
includes taxes & fees
Gorgeous Waterfront 3 Bedroom, 1.5 Bathroom Unit.
Terrace/patio
Living area
Exterior
Private kitchen
Exceptional
(16 reviews)

Spacious Modern Beach House, perfect for families

Branford

8% off
AU$6,332
for 7 nights, 1 home
AU$905 per night
includes taxes & fees
Spacious Modern Beach House, perfect for families
Pool
Dining
Private kitchen
Terrace/patio
Exceptional
(7 reviews)

Private Home - Pool and Close to CT Shoreline Beaches

North Branford

17% off
AU$14,118
for 7 nights, 1 home
AU$2,017 per night
includes taxes & fees
Private Home - Pool and Close to CT Shoreline Beaches
Welcoming living room for quiet conversations.
The new splash pad will be a hit with the little ones.
The Guilford train station is 1/3rd of a mile away. Need to be in the city?
Special sunsets overlook the harbor and the Lobster Pound.
Exceptional
(33 reviews)

Great home walkable to everything!

Guilford

8% off
AU$5,892
for 7 nights, 1 home
AU$842 per night
includes taxes & fees
Great home walkable to everything!
Dining
Terrace/patio
Room
Living area
Exceptional
(48 reviews)

4000+ SqFt Home. Amazing Views, Private, Close to Downtown and Yale Univeristy

East Haven

17% off
AU$5,963
for 7 nights, 1 home
AU$852 per night
includes taxes & fees
4000+ SqFt Home. Amazing Views, Private, Close to Downtown and Yale Univeristy
Exterior
Interior
Room
Interior
Wonderful
(32 reviews)

BEACH BUM CARRIAGE HOUSE with kayaks - steps to beach, park, marinas & brewery!

Branford

8% off
AU$3,075
for 7 nights, 1 home
AU$439 per night
includes taxes & fees
BEACH BUM CARRIAGE HOUSE with kayaks - steps to beach, park, marinas & brewery!
  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support
  • More quality time

    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less

    More space, more privacy, more amenities — more value

Find the perfect holiday rental for your Thimble Islands getaway

Learn about the unique charm of Thimble Islands with a stay in a holiday home rental. This city has something for everyone. If you need more space to accommodate a family holiday or a trip with friends, rental homes often come with separate dining areas and spacious living rooms.

Activities and attractions in and around Thimble Islands

Do you want to find things to do while you're in town? Venture out of your cosy holiday rental and check out everything that makes Thimble Islands a one-of-a-kind holiday spot. These are some of the most popular attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Bishops Orchard and Winery (4.2 mi / 6.7 km)
  • Rosabianca Vineyards (10.6 mi / 17.1 km)
  • Chamard Vineyards (11.5 mi / 18.5 km)
  • Chatfield Hollow State Park (11.8 mi / 18.9 km)
  • Yale Golf Course (12.9 mi / 20.8 km)
  • Gouveia Winery (13.1 mi / 21 km)

Exploring the natural features in Thimble Islands

Whether you're an active traveller or just want to appreciate the scenery, Thimble Islands is a great place to spend some time outside. Here are some of the area’s most eye-catching natural features, all within 30 miles (48.2 km) of the city centre:

  • Guilford Town Green (4.5 mi / 7.2 km)
  • East Haven Town Beach (5.9 mi / 9.6 km)
  • Lighthouse Point Park (7.6 mi / 12.2 km)
  • Sandy Point Beach (9.4 mi / 15.2 km)
  • New Haven Green (9.8 mi / 15.8 km)
  • Seabluff Beach (10.7 mi / 17.3 km)

Frequently asked questions

What is the most popular type of holiday home accommodation in Thimble Islands?
Houses are the most popular kind of holiday home in Thimble Islands, according to our data. Even if you've got something a little different in mind, Stayz has holiday homes in loads of sizes and shapes. Compare our options to find your perfect pad.
How much does it cost to rent a holiday home in Thimble Islands?
Different factors can influence what you'll pay for a holiday home in Thimble Islands, including the length of stay, season and type of property. Still, all of our holiday homes have something in common — incredible value. Just enter your travel dates to find your ideal fit.
How much does it cost to rent a beach house in Thimble Islands?
When you travel and the size and style of the property will determine the cost of your beachside stay. Put in your Thimble Islands travel dates to see all your options on Stayz. Did someone just say "private pool"? Use our filters to pick the features and amenities you need.
Are there pet-friendly holiday homes in Thimble Islands?
There certainly are. You'll have your pick of two holiday homes that welcome pets in Thimble Islands on Stayz. Our furry friends deserve a break too, so simply use our search function for pet-friendly holiday homes to book a perfect pad where your pooch can join in the fun.
What are popular home amenities in Thimble Islands?
When it comes to home amenities that people are searching for in Thimble Islands, a beach view, a barbecue grill and a water view rank the highest. With Stayz holiday homes, you'll discover options to match your style and taste, whether you're going on a trip with family members, friends or even pets.
Are there large group holiday homes in Thimble Islands?
With two Thimble Islands properties that can sleep five or more people, you can invite a few extra buddies or family members along. Whether you're planning a casual gathering or a birthday party, we'll help you find the ideal space to match the occasion.
Are there holiday homes in Thimble Islands that welcome kids?
Gather your entire family for fun-filled adventures in Thimble Islands at one of our two family-friendly holiday homes. These stays provide conveniences that are ideal for getaways with youngsters, including laundries, extra bedrooms and outdoor spaces. Simply check the "Properties good for families" filter and choose your favourite option.
What are the top attractions for families in Thimble Islands?
Keep the kids entertained at these leading family-friendly attractions in Thimble Islands:
  • East Haven Town Beach
  • Bill Miller's Castle
  • Lighthouse Point Park
How old do you have to be to rent a holiday home in Thimble Islands?
The minimum age is normally 16, 18 or 21. It can differ from one property to another on Stayz, so check the rules of your chosen Thimble Islands holiday home before booking your trip.
How long can I rent a holiday home in Thimble Islands for?
The amount of time you can book a Thimble Islands holiday home for differs depending on the property. Just enter your dates of travel to view options offering longer term stays. They come with all the things you need to make your extended break more enjoyable like air conditioning and laundries. Some holiday homes may also offer discounted weekly or monthly prices, so you can stay even longer for less.

More holiday ideas