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Holiday Homes in Woodbridge

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Check prices for these dates

Next weekend
8 Aug - 10 Aug
In two weeks
15 Aug - 17 Aug
In one month
29 Aug - 31 Aug
In two months
26 Sept - 28 Sept

Featured Holiday Homes in Woodbridge

Business or Weekend escape
Enjoy a refreshing swim under the stars at our pool, surrounded by a spacious deck.

Business or Weekend escape

9.2 out of 10, Wonderful, (42)
"Very nice owner with great communication. "
The price is AU$229
includes taxes & fees
4 Aug - 5 Aug
Business or Weekend escape
Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub
Enjoy a refreshing dip in the pool surrounded by a deck and basketball hoop.

Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub

10.0 out of 10, Exceptional, (136)
"Perfect location for a get-away! Beautiful location on the water. The cottage was cozy & had everything we needed. Very clean. Lots to do in the area. Host was very nice We had a great time and will absolutely be back! "
Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub
Cozy 3 bedroom minutes from Yale and the beach
Kitchen features a central island, oven, and white cabinetry with a patterned backsplash.

Cozy 3 bedroom minutes from Yale and the beach

7.0 out of 10, Good, (2)
"The inside was very clean, the back patio/garden area is cute, but the pool was green by day two. Overall we enjoyed our time here"
Cozy 3 bedroom minutes from Yale and the beach
Minutes to Walnut Beach, newly renovated 3 bedroom home
Enjoy a serene beachside retreat with a balcony overlooking the tranquil ocean.

Minutes to Walnut Beach, newly renovated 3 bedroom home

10.0 out of 10, Exceptional, (6)
"Very nice place."
Minutes to Walnut Beach, newly renovated 3 bedroom home
Charming 3-bedroom house with WiFi, AC in serene Fairfield
Enjoy cooking in this well-equipped kitchen with a large window offering a view of the outside.

Charming 3-bedroom house with WiFi, AC in serene Fairfield

9.6 out of 10, Exceptional, (4)
"Thank you for the stay!"
Charming 3-bedroom house with WiFi, AC in serene Fairfield
Steps to beach! Custom-built house with panoramic ocean views, wrap-around deck.
Guests can enjoy a serene beach experience with calm seas and fine sand.

Steps to beach! Custom-built house with panoramic ocean views, wrap-around deck.

10.0 out of 10, Exceptional, (47)
"Home was very comfortable and a great location. The views were spectacular. Owner gave us great recommendations for restaurants and nearby attractions. "
Steps to beach! Custom-built house with panoramic ocean views, wrap-around deck.
Cozy Lakefront Bungalow w firepit/dock/kayaks
Enjoy the view from the upper balcony, which offers a fire pit and Adirondack chairs in the yard.

Cozy Lakefront Bungalow w firepit/dock/kayaks

10.0 out of 10, Exceptional, (29)
"This is our second time visiting the area and staying at this beautiful home. It's close to many activities for children and adults, easy to access food and services and a beautiful overall area and home. We truly enjoy visiting!"
Cozy Lakefront Bungalow w firepit/dock/kayaks
Charming 2-bedroom house with WiFi, AC in Fairfield
Relax in a stylish living space with a geometric sculpture, potted plant, and modern sofa.

Charming 2-bedroom house with WiFi, AC in Fairfield

8.0 out of 10, Very good, (3)
"Amalfi’s place was as described. It was clean and comfortable and mostly quiet. Amalfi was excellent with communication. Would certainly stay again when visiting family."
The price is AU$540
includes taxes & fees
7 Aug - 8 Aug
Charming 2-bedroom house with WiFi, AC in Fairfield
The Daydreamer - Walk To Walnut Beach, Restaurant + Shops
Stunning marina views with boats docked, surrounded by beautifully lit buildings.

The Daydreamer - Walk To Walnut Beach, Restaurant + Shops

10.0 out of 10, Exceptional, (11)
"5 Star stay!"
The Daydreamer - Walk To Walnut Beach, Restaurant + Shops
Historic New England home ,Reunions Beach pass
Enjoy cooking and dining in this kitchen with a central island and dining table.

Historic New England home ,Reunions Beach pass

9.2 out of 10, Wonderful, (88)
"House was perfect for family get together. Enjoyed walking into town for afternoon shopping and dining."
The price is AU$1,032
includes taxes & fees
2 Sept - 3 Sept
Historic New England home ,Reunions Beach pass
Updated ranch Home 4 minutes from the beach on a quiet end street.
Enjoy cooking in this well-equipped kitchen with a microwave, toaster, and oven.

Updated ranch Home 4 minutes from the beach on a quiet end street.

8.4 out of 10, Very good, (7)
"It was everything that I expected. Fabian was very attentive and responsive. I would definitely rent again. "
Updated ranch Home 4 minutes from the beach on a quiet end street.
Dog-Friendly Oceanfront Getaway - Walk to Dining - Private Beach Access
Enjoy the ocean view from this room, featuring a sofa, chair, and small table.

Dog-Friendly Oceanfront Getaway - Walk to Dining - Private Beach Access

10.0 out of 10, Exceptional, (5)
The price is AU$1,084
includes taxes & fees
11 Aug - 12 Aug
Dog-Friendly Oceanfront Getaway - Walk to Dining - Private Beach Access
Lakeside/Sleeps20/HotTub/GameRoom/2Acres/Firepit
Enjoy a formal dining experience with a view of the surrounding forest from the large windows.

Lakeside/Sleeps20/HotTub/GameRoom/2Acres/Firepit

10.0 out of 10, Exceptional, (1)
Lakeside/Sleeps20/HotTub/GameRoom/2Acres/Firepit
42 Wood Ave · 5 Minute Walk To Beach! Amazing Backyard Space!
Relax in this stylish living room with a high ceiling, leather sofa, and comfortable armchair.

42 Wood Ave · 5 Minute Walk To Beach! Amazing Backyard Space!

8.6 out of 10, Excellent, (7)
"I rented this place because of the location and convenience to the many things we enjoy about Milford CT. The master bedroom is top-notch as well as the living space downstairs. We hoped to use the outdoor fire place make smores, but due to a medical emergency our trip was cut short. Regardless, we enjoyed our stay at 42 Wood Ave. Thank you, Tiffany, for supplying an awesome rental."
42 Wood Ave · 5 Minute Walk To Beach! Amazing Backyard Space!
Gorgeous 4BR Beach House with Private Beach Access.
Guests can enjoy beach access with a sandy shoreline and ocean views.

Gorgeous 4BR Beach House with Private Beach Access.

9.8 out of 10, Exceptional, (74)
"We loved our stay at this beautiful cottage. The entire experience was very smooth, from pre-check in to getting there and even offers to help with anything we needed in our stayThe cottage is very cozy and well-cared for. The rooms are comfortable and the Internet fast. There is a lot to do in the area, with New Haven nearby and many good restaurants."
Gorgeous 4BR Beach House with Private Beach Access.
Spacious Woodbury Home w/ Pool + Hot Tub!
Relax in a warm and inviting space with a hot tub, wicker furniture, and large windows.

Spacious Woodbury Home w/ Pool + Hot Tub!

8.0 out of 10, Very good, (3)
"Great spot and location, house was clean and enjoyable. Pool needs additional care and cleaning "
Spacious Woodbury Home w/ Pool + Hot Tub!
Centric property close to all the great things in the city
Enjoy a warm morning with a cup of coffee in the fully equipped kitchen.

Centric property close to all the great things in the city

7.6 out of 10, Good, (12)
"This rental was great accommodation"
The price is AU$471
includes taxes & fees
4 Aug - 5 Aug
Centric property close to all the great things in the city
Cozy 2 bedroom home located minutes from downtown
Kitchen features a central island, microwave, coffee maker, and dining table with four chairs.

Cozy 2 bedroom home located minutes from downtown

9.6 out of 10, Exceptional, (28)
"Perfect stay for the Yale-Harvard game. "
Cozy 2 bedroom home located minutes from downtown
The Jewel of The Cove - Historic Coastal Retreat
Enjoy a serene beach experience with sailboats on the calm sea and palm trees along the shoreline.

The Jewel of The Cove - Historic Coastal Retreat

2.0 star property
10.0 out of 10, Exceptional, (4)
"loved it so much, beautiful property 100 % would stay again "
The price is AU$812
includes taxes & fees
17 Aug - 18 Aug
The Jewel of The Cove - Historic Coastal Retreat
Dulce La Donna by the beach
Relax on the beach with comfortable lounge chairs and enjoy the ocean views.

Dulce La Donna by the beach

10.0 out of 10, Exceptional, (1)
"The owner is extremely welcoming and communicates very well. "
Dulce La Donna by the beach
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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