
Thimble Islands Holiday Rentals
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Our top choices for Thimble Islands holiday rentals

1. Bright Downtown Studio near Yale & East Rock!
Bright Downtown Studio near Yale & East Rock!
2. Yale Deluxe Modern Apartment
Yale Deluxe Modern Apartment
3. Château Blanc | Near Yale University
Château Blanc | Near Yale University
4. Cozy 1 King Bed | Smoking
Cozy 1 King Bed | Smoking
5. Relaxing 3-bedroom apartment in New Haven
Relaxing 3-bedroom apartment in New Haven
6. Yale Casa Verde Studio
Yale Casa Verde Studio
7. Modern Loft near Yale and Wooster Square + Parking
Modern Loft near Yale and Wooster Square + Parking
8. Cozy Home near private beach , close to New Haven area colleges Hospitals
Cozy Home near private beach , close to New Haven area colleges Hospitals
9. Stylish Wooster Square Home Walk to Yale
Stylish Wooster Square Home Walk to Yale
10. Spacious 2 Bedroom apartment close to Yale Bowl
Spacious 2 Bedroom apartment close to Yale Bowl
11. Luxury Studio Near Yale | Gym, W/D & Fast WiFi
Luxury Studio Near Yale | Gym, W/D & Fast WiFi
12. Yale Science Park 1BR | Free Parking
Yale Science Park 1BR | Free Parking
13. One bedroom in United States of America, New Haven
One bedroom in United States of America, New Haven
14. Cozy East Haven Home • Near Beach & Yale
Cozy East Haven Home • Near Beach & Yale
15. Stocked home close to Yale, in Heart of New Haven
Stocked home close to Yale, in Heart of New Haven
16. Great 3 Bedroom close to downtown and Yale!
Great 3 Bedroom close to downtown and Yale!
17. New Haven 2BR near Yale | Rooftop, Gym, Garage & Laundry
New Haven 2BR near Yale | Rooftop, Gym, Garage & Laundry
18. Spacious Stay Downtown New Haven
Spacious Stay Downtown New Haven
19. Modern Elegant Stay by Yale • Gym • Rooftop Terrace
Modern Elegant Stay by Yale • Gym • Rooftop Terrace
20. Nautical 3BR Sleeps 8 @ Tweed Airport W/ Fire Pit + Smart TVs Near Beach & Yale
Nautical 3BR Sleeps 8 @ Tweed Airport W/ Fire Pit + Smart TVs Near Beach & YaleFind holiday rentals that suit your style
Top Thimble Islands Hotel Reviews

Omni New Haven Hotel at Yale
Find out more about Thimble Islands
You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Thimble Islands holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.
As much as you love your vacation rental, it’s always good to get out and explore to soak up Thimble Islands. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Thimble Islands. Seeing all the best attractions is bound to make you fall in love with Thimble Islands. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.
It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Thimble Islands short-term rentals, that won’t be hard to do.
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- Bill Miller’s Castle
- Wharton Brook State Park
- Art Plus Studio
- Acme Mall Shopping Center
- Connecticut Sportsplex
- New Haven Holidays
- Putnam Place Shopping Center
- Yale-New Haven Hospital
- Branford Hills Plaza Shopping Center
- Anna Mia's
- Sterling Memorial Library at Yale University
- Yale Bowl
- Quinnipiac University
- Stony Creek Brewery
- Yale University
- Visit East Rock
- Visit Northford
- Visit Long Wharf
- Visit Killingworth
- Visit New Haven
- Visit Mill River
































































