Top Cottages in New Haven County in 2026

New Haven County Cottages
Connecticut
United States of America
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Top Cities in New Haven County

A church with a tall spire, surrounded by trees and a stone bridge.

Wallingford

Our top choices for New Haven County cottages

A seaside patio with white wicker chairs, a table, and a beige umbrella.

A deck with a table and chairs, a covered grill, and a beach view.

A pebble beach with kayaks and a blue chair.

A spacious living room with a large sliding glass door leading to a balcony with a view of the ocean. There are multiple seating areas, a flat-screen TV mounted on the wall, and a ceiling fan.

1. Charming 3 Bedroom Beach Front Cottage

Charming 3 Bedroom Beach Front Cottage

Milford

9.4 out of 10, Exceptional, (19 reviews)

9.4/10

Exceptional

(19 reviews)

"Beautiful location and worked very well for our trip to visit with family in the areas over Thanksgiving."

David S.

Charming 3 Bedroom Beach Front Cottage

A coastal residential area with houses, a beach, and a pier.

A spacious living area with a large window overlooking the sea, a fireplace, and a dining table set with placemats.

A coastal beach with a concrete walkway, large rocks, and a grassy area.

A screened patio with outdoor seating, a small table, and a view of the ocean.

2. Direct waterfront renovated cottage.

Direct waterfront renovated cottage.

Madison Center

10.0 out of 10, Exceptional, (100 reviews)

10/10

Exceptional

(100 reviews)

"Unbeatable views and professional hosts."

Russell A.

Direct waterfront renovated cottage.

A white house with green shutters, a front porch, and a garage.

A spacious living room with a fireplace, a staircase, and a large window.

A spacious living room with a large L-shaped sectional sofa, a flat-screen TV, and a stone fireplace.

A modern kitchen with white cabinets, stainless steel appliances, and a wooden floor.

3. 2 Mi to Dtwn: 2-acre Retreat w/ Large Yard!

2 Mi to Dtwn: 2-acre Retreat w/ Large Yard!

3.0 star property

Madison

10.0 out of 10, Exceptional, (1 review)

10/10

Exceptional

(1 review)

"Excellent. The property was simply lovely and the owner was excellent to work with. Location was just what we were looking for, the yard was large and landscaping & outdoor areas were wonderful. Thank you!"

Cindie

2 Mi to Dtwn: 2-acre Retreat w/ Large Yard!

A two-story house with a deck overlooking a body of water, stone steps leading to the entrance, and a stone wall.

A kitchen with large windows, a dining area with chairs, and a view of a body of water.

A dining table set on a deck with a view of the water, featuring a white tablecloth, woven placemats, and candles.

A bedroom with a large window, a bed, a chair, and a view of a body of water.

4. Waterfront Cottage in Branford

Waterfront Cottage in Branford

branford

10.0 out of 10, Exceptional, (110 reviews)

10/10

Exceptional

(110 reviews)

"Beautiful Property "

Todd M.

Waterfront Cottage in Branford

A building with a large sign, a flag, and a small garden area.

A spacious living room with a large flat-screen TV, a wooden coffee table, a white sofa, and a patterned rug.

A room with a wooden floor, a wicker chair with a leaf-pattern pillow, a potted plant, and a view of a house through large windows.

5. Beachside Branford- walk to Beach, Grill

Beachside Branford- walk to Beach, Grill

Pine Orchard

9.6 out of 10, Exceptional, (9 reviews)

9.6/10

Exceptional

(9 reviews)

"Charming little cottage that was just right for our trip to the CT shoreline."

Alex S.

Beachside Branford- walk to Beach, Grill

A living room with a beige sofa, a glass coffee table, and a staircase in the background.

A living room with a beige sofa, a glass coffee table, and a chandelier.

A cozy living room with a sofa, a pink throw blanket, and a radiator.

A dining area with a glass table, white chairs, a chandelier, and a vase with pampas grass.

6. Charming Connecticut Retreat Near Museums & Hiking

Charming Connecticut Retreat Near Museums & Hiking

3.0 star property

Waterbury

Charming Connecticut Retreat Near Museums & Hiking

A rustic barn-style building with a green door and windows, surrounded by trees and a gravel driveway.

A spacious kitchen with a large island, a dining area, and a bedroom with a balcony.

A spacious living room with a high ceiling, a ceiling fan, and a large window.

A modern kitchen with a central island, wooden stools, a stainless steel refrigerator, and a water dispenser.

7. Guilford Carriage House at Granite Lodge!

Guilford Carriage House at Granite Lodge!

3.0 star property

Guilford

9.0 out of 10, Wonderful, (2 reviews)

9.0/10

Wonderful

(2 reviews)

"I’m normally not one to leave reviews but I had to for The Carriage House! Everything from the homey, relaxing feel to the great views was amazing! My friends and I wanted to extend our stay lol. We’re already planning another stay here for a summer trip! Also appreciated the host’s friendliness and ensuring we had an enjoyable experience. 10/10"

Anonymous traveler

Guilford Carriage House at Granite Lodge!

A two-story house with a front porch and a small garden.

A residential lawn with a lawnmower, a barbecue grill, and a wooden board game.

A bedroom with a bed, a ceiling fan, and a window.

A kitchen with white cabinets, a microwave, a sink, and a stove.

8. Settle In for Winter: East Haven Extended Stay

Settle In for Winter: East Haven Extended Stay

3.0 star property

Momauguin

10.0 out of 10, Exceptional, (2 reviews)

10/10

Exceptional

(2 reviews)

"This was a fantastic property in a great location. We were able to walk to nearby restaurants. We were there in the off season but enjoyed walking along the beach which is so close. "

Elizabeth

Settle In for Winter: East Haven Extended Stay

A wooden deck with a pool, lounge chairs, and a view of neighboring houses.

A modern living room with a wooden dining table, white chairs, a grey sofa, and a staircase with bamboo decor.

A beach with palm trees, a wooden boardwalk, and a clear blue sky.

A modern kitchen with wooden cabinets, a marble countertop, and a built-in oven.

9. Near Yale & Lighthouse Point Beach: Home w/ Pool!

Near Yale & Lighthouse Point Beach: Home w/ Pool!

3.0 star property

East Shore

Near Yale & Lighthouse Point Beach: Home w/ Pool!

A two-story house with a porch, a mailbox, and a lawn.

A beach with a house in the background, a clear sky, and a calm sea.

A wooden beach gazebo with a view of the ocean.

A garden with a wooden bridge, a pond, and a stone wall.

10. Welcoming 1-Bedroom Cottage in Charming Madison is One Mile to Town and Beach!

Welcoming 1-Bedroom Cottage in Charming Madison is One Mile to Town and Beach!

Madison

9.4 out of 10, Exceptional, (3 reviews)

9.4/10

Exceptional

(3 reviews)

"Cozy cottage was perfect for our long weekend in Madison!"

Samantha D.

The price is AED 549

AED 549

AED 1,295 total

includes taxes & fees

20 Oct - 21 Oct

Welcoming 1-Bedroom Cottage in Charming Madison is One Mile to Town and Beach!

A two-story house with a covered porch, a front door, and a small outdoor seating area with a table and chairs.

A living room with a wooden floor, a white sofa, a table with a vase of flowers, a fireplace, and a television on a stand.

A house with a porch, steps, and a mailbox.

A waterfront property with a dock, boats, and a building with a large window.

11. Cozy Home near private beach , close to New Haven area colleges Hospitals

Cozy Home near private beach , close to New Haven area colleges Hospitals

Branford

9.4 out of 10, Exceptional, (83 reviews)

9.4/10

Exceptional

(83 reviews)

"Property was clean with some nice cozy touches. Wine on the table, fruit in the frig, chocolate for comfort, coffee for wakeup. Host was very pleasant and accommodating. Will definitely stay there again."

Vincent

The price is AED 410

AED 410

AED 1,117 total

includes taxes & fees

21 Oct - 22 Oct

Cozy Home near private beach , close to New Haven area colleges Hospitals

A kitchen with white cabinets, a black refrigerator, a double sink, and a window overlooking a wooded area.

A bathroom with a shower, toilet, sink, and patterned floor.

A living room with a dark grey sectional sofa, two patterned armchairs, a round coffee table with a plant, and a grey bench.

A kitchen with white cabinets, a black refrigerator, a stove, and a sink.

12. Serene Country Cottage

Serene Country Cottage

Woodbridge

8.0 out of 10, Very good, (11 reviews)

8.0/10

Very good

(11 reviews)

"We had a great one night stay here! The place is really cute, clean and comfortable. One of the greatest parts about the stay was the host, Trent. He was welcoming and VERY responsive to questions! "

felicia

The price is AED 475

AED 475

AED 799 total

includes taxes & fees

19 Oct - 20 Oct

Serene Country Cottage

A wooden house with a porch, a small deck, and a gravel yard.

A kitchen pantry with shelves stocked with jars, spices, and kitchenware.

A modern living room with a sectional sofa, a round coffee table, and a dining area with a wooden table and chairs.

A modern bathroom with a glass shower enclosure, white tiled walls, a large mirror, and a window.

13. Modern 4 Bedroom Beach House: Ideal for Families & Long Stays

Modern 4 Bedroom Beach House: Ideal for Families & Long Stays

West Haven

9.6 out of 10, Exceptional, (15 reviews)

9.6/10

Exceptional

(15 reviews)

"Great option over multiple hotel rooms for my sibs and me.Allowed us to be together in comfort.Thanks Tom!"

David G.

Modern 4 Bedroom Beach House: Ideal for Families & Long Stays

An aerial view of a coastal residential area with houses, a bridge, and a body of water.

A covered porch with a wicker sofa and chairs, large windows, and a view of greenery.

A spacious room with wooden floors, large windows, wicker furniture, a fireplace, and a bookshelf.

A rustic kitchen with wooden beams, a dining area with chairs, and a view to the outside.

14. 1930s Waterfront Cottage on Tuttle's Point

1930s Waterfront Cottage on Tuttle's Point

Guilford

9.6 out of 10, Exceptional, (33 reviews)

9.6/10

Exceptional

(33 reviews)

"All around nice old fashioned Summer vacation neighborhood."

Vicki M.

1930s Waterfront Cottage on Tuttle's Point

A beachside property with a large house featuring a wrap-around porch, a sandy beach, and a tree.

A covered porch with a wooden floor, a white table, and two floral-patterned chairs.

A beachside room with a view of the beach, a table with a vase of flowers, and a chair.

A beach with four lounge chairs facing the ocean, a clear sky, and a distant shoreline.

15. Beachfront Connecticut Retreat w/ Views!

Beachfront Connecticut Retreat w/ Views!

Milford

9.2 out of 10, Wonderful, (10 reviews)

9.2/10

Wonderful

(10 reviews)

"The owner of the house is very nice and accommodating"

Miriam J.

Beachfront Connecticut Retreat w/ Views!

A small, single-story building with a green door and windows, surrounded by a stone wall and vegetation.

A dining area with a table set for six, surrounded by wooden chairs, a chandelier, and a large window.

16. Guilford Carriage House at Granite Lodge!

Guilford Carriage House at Granite Lodge!

Guilford

10.0 out of 10, Exceptional, (19 reviews)

10/10

Exceptional

(19 reviews)

"Cute place, comfy beds, had everything we needed!"

parnpa

Guilford Carriage House at Granite Lodge!

A beach with calm waters and a distant island.

A dining area with a table, two chairs, a window with blinds, and a view of a building outside.

A narrow paved pathway between two buildings with a sign indicating '718 East Broadway'.

A shower area with a glass door, a tiled wall, and a shelf with toiletries.

17. Renovated Milford Beach home by Charles Island/Silver Sands Pk

Renovated Milford Beach home by Charles Island/Silver Sands Pk

Milford

10.0 out of 10, Exceptional, (11 reviews)

10/10

Exceptional

(11 reviews)

"Susana is fantastic, location is perfect for us, unit is great in cleanliness, amenities and accommodations. "

Michelle P.

Renovated Milford Beach home by Charles Island/Silver Sands Pk

A living room with a wooden cabinet, a grey sofa, a coffee table, and a painting on the wall.

A compact room with a bed, a washing machine, and two paintings on the wall.

A kitchen with white cabinetry, a black refrigerator, and a wooden countertop.

A small, single-story house with a front porch, a black door, and two windows with shutters.

18. Historic Whitneyville Cottage

Historic Whitneyville Cottage

Hamden

9.0 out of 10, Wonderful, (19 reviews)

9.0/10

Wonderful

(19 reviews)

"Great place, small and cozy, perfect for a weekend getaway, with great hosts. Would highly recommend!"

Uriah M.

Historic Whitneyville Cottage

A two-story house with a front porch, a welcome sign, and a flag.

A dining area with a wooden table, white chairs, and a chandelier.

A sandy beach with a dock and sailboats.

A sand sculpture of a beach with the words "SHORT BEACH" written on it.

19. Short Beach Coastal Cottage

Short Beach Coastal Cottage

Branford

10.0 out of 10, Exceptional, (25 reviews)

10/10

Exceptional

(25 reviews)

"Great location, exactly as advertised. Perfect for us while in the area for a wedding."

Ann R.

Short Beach Coastal Cottage

A two-story house with a porch, a white picket fence, and a well-maintained lawn.

A patio area with a white lattice arbor, outdoor furniture, and potted plants.

A living room with a blue sofa, a wooden coffee table, and a patterned rug.

A beach with a sandy shore and a few houses in the background.

20. Available July 1, 2025 2 week or monthly.

Available July 1, 2025 2 week or monthly.

Madison

Available July 1, 2025 2 week or monthly.

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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