Thimble Islands Vacation Homes

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Our top choices for Thimble Islands holiday homes

A living room with a dark grey sofa, a wooden coffee table with a vase of white flowers, a patterned rug, and a ceiling fan.

1. Cozy East Haven Home • Near Beach & Yale

Momauguin

Sarah S.

A modern living room with a gray sofa, a dining table with white chairs, a small coffee table, and a potted plant.

2. Gorgeous Waterfront 2 Bedroom 1 Bath Modern Home.

Fair Haven

Jamie S.

HK$1,720 total

includes taxes & fees

30 Nov - 1 Dec

A living room with a staircase, a sofa, a coffee table, and a TV.

3. Loft •Pool • Gym • Free Parking • Near Yale

Orange

Ali B.

HK$1,927 total

includes taxes & fees

9 Nov - 10 Nov

A spacious living room with a grey sectional sofa, a small ottoman, and a large window with a view.

4. Gorgeous Waterfront 3 Bedroom, 1.5 Bathroom Unit.

Fair Haven

Wallace R.

HK$2,393 total

includes taxes & fees

30 Nov - 1 Dec

A modern living room with a sofa, coffee table, and a TV mounted on the wall.

5. Once the old Schools house now a newly furnished Apartment

Wallingford Center

Jeanette W.

HK$2,280 total

includes taxes & fees

12 Nov - 13 Nov

A modern kitchen with a stainless steel refrigerator, wooden beams, a dining area with a table and chairs, and a large window with blinds.

6. Coastal Landing Stay

East Shore

HK$3,786 total

includes taxes & fees

9 Nov - 10 Nov

A staircase with dark wooden steps and black balusters, a round mirror on the wall, a blue armchair, a wicker basket with flowers, and a floor lamp.

7. Las Casitas Retreat

East Shore

Tim H.

HK$5,324 total

includes taxes & fees

9 Nov - 10 Nov

A living room with a sofa, a coffee table, a TV, and a lamp.

8. Quiet 1st-Floor 2BR Haven w/ King Bed, Desks, In-Unit Laundry & 2-Car Parking | Walk to Yale

Newhallville

HK$3,118 total

includes taxes & fees

9 Nov - 10 Nov

A modern kitchen with white cabinetry, a central island with stools, pendant lighting, and a view to an outdoor area.

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

East Shore

Zach P.

HK$5,548 total

includes taxes & fees

9 Nov - 10 Nov

A covered porch with a wicker chair and a potted plant.

10. 3-bedroom house just walking distance from Yale and Downtown

Dixwell

Mark S.

HK$3,133 total

includes taxes & fees

9 Nov - 10 Nov

A covered patio with a glass table, white metal chairs, a green sofa, and a white metal bench.

11. Historic New England home ,Reunions Beach pass

Guilford

Dr. Maureen C.

HK$4,814 total

includes taxes & fees

9 Nov - 10 Nov

A modern kitchen with a granite island, stainless steel appliances, and a bar area with bar stools.

12. Beachside Bliss w/ Game Room, Gym & Golf Green

Westbrook

Morgan M.

HK$4,697 total

includes taxes & fees

1 Dec - 2 Dec

A wooden deck with a table and chairs, overlooking a river and trees.

13. Steps to Beach • Hot Tub • Game Room • Water Views

Branford

HK$9,690 total

includes taxes & fees

9 Nov - 10 Nov

A modern kitchen with white cabinets, stainless steel appliances, and a black oven.

14. Renovated Beachside Retreat

Milford

Michelle D.

HK$3,396 total

includes taxes & fees

12 Nov - 13 Nov

A spacious living room with a grey sectional sofa, two windows with blinds, and a ceiling light fixture.

15. Gorgeous Waterfront 2:1 - 2 houses in 1 building.

Fair Haven

HK$5,858 total

includes taxes & fees

9 Nov - 10 Nov

A modern living room with hardwood flooring, a leather sofa, a round coffee table, and a wooden side table. There is a dining area with a table and chairs visible in the background.

16. Luxurious-Modern feel w/ custom features - AC, short walk to Shelton

Shelton

HK$3,573 total

includes taxes & fees

9 Nov - 10 Nov

Lovely spacious kitchen to cook and enjoy your meals; Large island to sit and eat.

17. Heavenly Home in New Haven /5 mins drive from Yale

Fair Haven

Aliza T.

HK$5,818 total

includes taxes & fees

22 Nov - 23 Nov

A modern kitchen with a marble island, bar stools, and a dining area with a table and chairs.

18. Luxe, designer renovation; walk to Tyde wedding venue, shops & beach!

Milford

Traci F.

HK$3,383 total

includes taxes & fees

11 Nov - 12 Nov

A living room with a fireplace, a sofa, a coffee table, and a cabinet.

19. Great Hammcock Getaway, cozy home, hot tub, fire pit, beaches nearby.

Old Saybrook

Karol T.

HK$3,767 total

includes taxes & fees

10 Nov - 11 Nov

A modern living room with a large TV, white cabinetry, and a view of the outdoors.

20. Charming beach home, complete with pool & cozy guest house!

Clinton

Juliana A.

HK$10,232 total

includes taxes & fees

12 Nov - 13 Nov

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Top Thimble Islands Hotel Reviews

Red Roof Inn Milford - New Haven

10/10 Excellent

"good for the price. the older gentleman working the front was really kind and the room was clean."

Clarion Inn North Haven - New Haven North

10/10 Excellent

"At the time of our visit, the hotel was doing major remodeling, so the property was not as nice as I'm sure it's going to be. The wing where our room was had been finished and was a great upgrade. The only real concern about our stay is in the bathroom. The shower faucet was quite difficult to regulate and the trim rim was loose which will allow the water to ruin the new remodel. Good breakfast with many choices, delightful staff, and kept well stocked. Would definitely recommend this hotel as it was not a far drive from Yale."

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