Holiday houses in Woodbridge

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Top-rated holiday rentals in Woodbridge

Guests agree: these stays are highly rated for location, cleanliness and more.

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Guest favourite

Apartment in Milford

4.97 out of 5 average rating, 512 reviews

Water front studio apartment with fireplace.

This is a beautifully appointed studio apartment located off the patio level of a water front home. Guests enjoy a large private patio over looking gorgeous sweeping views of Long Island Sound. A private entrance and off street parking. The amazing views and amenities make this space the perfect romantic getaway! Close to I95 and Metro North railroad. Ten minutes to great dining in downtown Milford. A true waterfront oasis! Come and experience this beautiful retreat! You won't be disappointed!

22–29 Oct

$398 NZD per night

Guest favourite

Home in North Haven

5.0 out of 5 average rating, 123 reviews

Luxury Stay in Expansive Historical Home

The Bassett House, originally built in 1802, this large historic farmhouse was elegantly remolded in 2018. North Haven, CT is centrally located and just minutes from Yale, Quinnipiac, UNH, and SCSU as well as shopping, the best restaurants, hiking trails state parks and beaches, and many local attractions including various vineyards. If you’re planning a business trip or a gathering for family or friends, then our home can provide you with an exceptional level of comfort during your time in CT!

16–23 Sep

$1,660 NZD per night

Guest favourite

Guest suite in Wallingford

5.0 out of 5 average rating, 502 reviews

Wintergreen Gardens Suite @ William Becroft House

LGBTQ friendly. Our 1915 Arts & Crafts bungalow's spacious in-law suite offers driveway parking, pvt. entrance, sunroom, king bedroom, en-suite bath, kitchenette w/fridge, micro, coffee maker, toaster. Relax in bed with 40" HDTV with Amazon Prime, HBO Max, Netflix, premium cable. Enjoy private gardens to sun, read a book or cup of coffee. Short drive to 4 Vineyards, Theater and the train station. Coming for a special event? Book an appointment at our salon, Jimmy James Salon. Ask for info.

31 Jan – 7 Feb

$166 NZD per night

Guest favourite

Home in New Haven

4.99 out of 5 average rating, 171 reviews

Historic New Haven Home

Our family owned New Haven vacation house is a renovated 1920s Tudor. It's located in a quiet, safe, & beautiful neighborhood, close to downtown and Yale. We've carefully preserved historic aspects we love (ie: art deco tile & leaded glass windows), and combined it with central a/c, USB ports, new appliances, gas fireplace, high speed wifi & more. You’re also welcome to use the small screened in porch, patio with chairs, and the yard. The entire house and driveway is yours when you rent.

8–15 Jun

$424 NZD per night

Guest favourite

Apartment in Brookfield

4.94 out of 5 average rating, 186 reviews

Peaceful apartment on 3.5 acres w/ Artist studio.

Welcome to our cozy apartment! This fully enclosed apartment is attached to our main house on a beautiful 3.5-acre property in Brookfield. Enjoy a kitchen, comfortable living and bedroom area, and a clean bathroom. Guests have access to a shared 32 ft, 10 ft deep pool, artist studio, pool table,, garden, fire space, and outdoor seating. We provide a guidebook for your convenience. Book now and experience a perfect blend of comfort, creativity, and relaxation.

16–23 Mar

$228 NZD per night

Guest favourite

Guest suite in Hamden

4.96 out of 5 average rating, 715 reviews

Large Private Studio + Entrance + Bath

Large beautiful secluded studio with a private entry and private bath. Includes comfy queen size bed, futon sofa bed, free wifi, large TV with tons of movies, eat-in table, microwave, mini-fridge, Keurig, closet w/ iron, and your own dedicated room temperature controls. Located in a beautiful, safe, and quiet neighborhood, the studio is attached to a split level house and located in the back on the lower level. It overlooks beautiful woodlands.

5–12 Jul

$331 NZD per night

Guest favourite

Guest suite in Shelton

4.81 out of 5 average rating, 264 reviews

Super cozy 1 BR apt. own entrance, great loc.

Very quiet residential neighborhood, very clean, super cozy apartment with two bedrooms, living room; computer desk with work station, kitchenette (no stove), own bathroom, and amenities. 20 minutes away from Bridgeport, 15 minutes away from Yale, New Haven. Lakes in walking distance, Metro-North rail; 7 minutes, local shopping area 1 mile. Bus route in walking distance. Great neighborhood!! All are welcomed. Warm community.

25 Apr – 2 May

$124 NZD per night

Guest favourite

Guesthouse in New Haven

4.94 out of 5 average rating, 241 reviews

Square 6ix

Inviting, eclectic, and completely private, this single family stand-alone guest house is an intimate and engaging haven. Stylishly decorated with mid-century modern furniture and adorned with pieces from local artists, this quiet home has a separate entrance, separate porch, high ceilings, and a fully equipped kitchen. The guest house is located a walking-block away from the charms of Westville Village and Edgewood Park.

27 Aug – 3 Sep

$440 NZD per night

Guest favourite

Apartment in New Haven

4.93 out of 5 average rating, 194 reviews

Perfect for Yale and New Haven Visits

We purchased the house containing this apartment in 2017, and have been steadily updating and modernizing the space. Beautiful, recently refreshed apartment in a circa 1895 Victorian home. Hardwood floors throughout, and newly redone kitchen and bathroom. Ideally located in a historic neighborhood, with easy access to Yale University and athletic fields, Westville Music Bowl, Hopkins school, and Downtown New Haven.

3–10 Jan

$325 NZD per night

Guest favourite

Apartment in West Haven

4.9 out of 5 average rating, 424 reviews

! ! ! entire apartment close to the beach ! !

Come and experience West Haven and the Long Island Sound in this nice and cozy apartment close to the beach. Our apartment is complete with a full-size kitchen, bathroom, cable TV, laundry room, fresh linens, towels, air conditioning, wide driveway, and free WiFi. We will provide some FREE complimentary snacks. This apartment is ideal for single travelers, couples, and can accommodate up to three people (adults only).

20–27 Apr

$193 NZD per night

Guest favourite

Home in New Haven

4.92 out of 5 average rating, 173 reviews

Large Designer Westville house! Walk to Yale Bowl

Large pristine 2 bedroom, perfect location, set up specifically for the luxury traveler. Central a/c and heat. Cozy common areas with extra large, well-stocked kitchen, huge dining table, comfortable and very quiet bedrooms with black out curtains, memory foam mattresses (Tuft & Needle), and super soft sheets. Centrally located house with all the amenities of home. Safe and quiet, cute walkable area!

1–8 Jun

$400 NZD per night

Guest favourite

Home in Cheshire

5.0 out of 5 average rating, 118 reviews

Pool House

The Pool House is a one bedroom that is fully furnished with all the amenities you would need. There is a queen size bed and a sofa in the living room that pulls out to a full size bed. Fully equipped kitchen, dinning room and living room area. Washer and dryer. Heated pool with large patio and deck. Outdoor refrigerator and gas grill.

15–22 Apr

$282 NZD per night