Vacation rentals in Woodbridge

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Top-rated vacation rentals in Woodbridge

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Guest favorite

Apartment in Milford

4.97 out of 5 average rating, 510 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!

Sep 26 – Oct 3

R3,839 ZAR per night

Guest favorite

Apartment in New Haven

4.99 out of 5 average rating, 114 reviews

Bright 1 BR Apt Steps From Yale

Enjoy a bright and cozy 1 bedroom apartment just 2 blocks from the Yale campus and The Shops at Yale. Located in a 3 unit brick building, designated as a property on The National Register of Historic Places, this small renovated 2nd floor apartment maintains the characteristics of the building's original design, while providing all amenities needed for a comfortable stay. Convenient free off street parking provided. Great shops, restaurants, nightlife, and museums can all be accessed by foot.

Nov 27 – Dec 4

R2,491 ZAR per night

Guest favorite

Guesthouse in Southbury

4.93 out of 5 average rating, 266 reviews

Charming Guest Cottage with Modern Amenities

Private Guest House set on 5+ Acres, along with Historic Colonial Home. Bright and sunny and over looks pool and gardens (seasonal). Efficiency with Kitchen featuring 2 burner stove, Microwave, Under Counter Fridge/Freezer/Ice Maker, Dishwasher, Granite Counters. . Dining Area, Great Room w/ soaring ceilings, French Doors to private patio, hardwood floors. Loft with full-sized bed, and sofa can be a to Queen Size Sleeper. Full bath with extra-large shower. Dog friendly (approval needed).

Aug 2 – 9

R2,959 ZAR per night

Guest favorite

Guest suite in Wallingford

5.0 out of 5 average rating, 499 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.

Mar 20 – 27

R1,668 ZAR per night

Guest favorite

Cottage in Easton

4.98 out of 5 average rating, 190 reviews

Cozy Modern Cottage with Fireplace

Clean, modern + large, our guest house has all the amenities and comforts of home. Cottage is dressed in whites and neutrals with natural light and plants throughout for a sacred, restful feel. Full kitchen, king bed, gas fireplace, laundry and spacious grounds with meditation hill, fire pit, stone fences, and nearby hiking trails. Pool and hot tub May-Sept. Come relax in New England's stunning natural beauty. Read our photo captions for more details. We look forward to meeting you!

May 3 – 10

R2,394 ZAR per night

Guest favorite

Apartment in Brookfield

4.94 out of 5 average rating, 184 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.

Sep 17 – 24

R2,335 ZAR per night

Guest favorite

Guest suite in Hamden

4.96 out of 5 average rating, 713 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.

Jun 18 – 25

R3,238 ZAR per night

Guest favorite

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.

Jan 6 – 13

R1,184 ZAR per night

Guest favorite

Guesthouse in New Haven

4.94 out of 5 average rating, 240 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.

Aug 20 – 27

R3,900 ZAR per night

Guest favorite

Apartment in New Haven

4.93 out of 5 average rating, 192 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.

Sep 21 – 28

R3,060 ZAR per night

Guest favorite

Guest suite in Morris

4.99 out of 5 average rating, 341 reviews

Lakeside Private Guest Suite

Feel like you're in your own studio apartment in the spacious, bright lower level of our home! Walk out to your own private lounging/dining area. Separate entrance and parking space. Enjoy the serenity of Camp Columbia state park, as it is our extended backyard. Tip: The sunsets are beautiful! 2 hours from NYC, 30-45 minutes to local skiing and just 10 minutes to Washington Depot.

Mar 23 – 30

R1,790 ZAR per night

Guest favorite

Home in Cheshire

5.0 out of 5 average rating, 117 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.

Nov 26 – Dec 3

R2,759 ZAR per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Woodbridge vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Woodbridge's top sights

Westville Music Bowl6 locals recommend

Yale Bowl16 locals recommend

Bella's Cafe32 locals recommend

Five Guys4 locals recommend

Super Stop & Shop14 locals recommend

Starbucks11 locals recommend

Other great vacation rentals in Woodbridge

Guest favorite

Tiny home in Ansonia

5.0 out of 5 average rating, 13 reviews

Cozy Tiny Home for Solo Travelers Near Everything

Sep 24 – Oct 1

R1,745 ZAR per night

Superhost

Apartment in West Haven

4.86 out of 5 average rating, 28 reviews

Beautiful New Studio Close to Yale!

Feb 25 – Mar 4

R1,895 ZAR per night

Guest favorite

Apartment in Hamden

4.88 out of 5 average rating, 17 reviews

Welcoming & Clean Condo near Hamden Shopping

Feb 4 – 11

R2,224 ZAR per night

Guest favorite

Guest suite in New Haven

4.88 out of 5 average rating, 32 reviews

The West Rock “Tree-House”

May 31 – Jun 7

R2,344 ZAR per night

Guest favorite

Guest suite in Hamden

4.95 out of 5 average rating, 39 reviews

Spacious basement suite with private entrance

May 2 – 9

R2,003 ZAR per night

Guest favorite

Condo in Hamden

5.0 out of 5 average rating, 8 reviews

Cozy 1 bedroom apartment, great location.

Feb 6 – 13

R2,305 ZAR per night

Guest favorite

Guest suite in Northford

5.0 out of 5 average rating, 13 reviews

Private Bright Studio Retreat with kitchen

Aug 24 – 31

R1,726 ZAR per night

Guest favorite

Apartment in Middlebury

4.98 out of 5 average rating, 64 reviews

Cozy Apartment with Water View of Brook

Jun 26 – Jul 3

R1,962 ZAR per night

Show all

Quick stats about vacation rentals in Woodbridge

Total rentals
60 properties
Wifi availability
60 properties include access to wifi
Rentals with dedicated workspaces
30 properties have a dedicated workspace
Pet-friendly rentals
10 properties allow pets
Family-friendly rentals
20 properties are a good fit for families
Total number of reviews
2.2K reviews

Frequently Asked Questions

Do house rentals in Woodbridge have wifi?
Absolutely! We offer over 30 house rentals with wifi in Woodbridge. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly vacation rentals in Woodbridge?
Woodbridge has more than 20 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
Do house rentals in Woodbridge have a kitchen?
Absolutely! We offer over 30 house rentals with a kitchen in Woodbridge. Enjoy a tailored experience with all the comforts you desire.
Are there pet-friendly vacation rentals in Woodbridge?
Four-legged friends are welcome in Woodbridge. Choose from more than 10 vacation rentals for guests traveling with pets.
Do house rentals in Woodbridge have air conditioning?
Absolutely! We offer over 20 house rentals with air conditioning in Woodbridge. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Woodbridge have free parking?
Absolutely! We offer over 30 house rentals with free parking in Woodbridge. Enjoy a tailored experience with all the comforts you desire.
Are there vacation rentals with a dedicated workspace in Woodbridge?
Yes! Work meets play with ease at over 30 vacation rentals in Woodbridge featuring dedicated workspaces. Stay connected and productive in your home away from home.
Where should I stay in Woodbridge?
Make yourself at home in Woodbridge by choosing from our most frequently booked neighborhoods. We have over 1,020 vacation rentals in West Rock, over 1,060 vacation rentals in West New Haven, and over 980 vacation rentals in Westville.

Vacation rentals in Woodbridge

Top-rated vacation rentals in Woodbridge

Vacation rentals for every style

Houses

Hotels

Unique stays

Popular amenities for Woodbridge vacation rentals

Stay near Woodbridge's top sights

Other great vacation rentals in Woodbridge

Tiny home in Ansonia

Apartment in West Haven

Apartment in Hamden

Guest suite in New Haven

Guest suite in Hamden

Condo in Hamden

Guest suite in Northford

Apartment in Middlebury

Quick stats about vacation rentals in Woodbridge

Total rentals

Wifi availability

Rentals with dedicated workspaces

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Frequently Asked Questions

Do house rentals in Woodbridge have wifi?

Are there family-friendly vacation rentals in Woodbridge?

Do house rentals in Woodbridge have a kitchen?

Are there pet-friendly vacation rentals in Woodbridge?

Do house rentals in Woodbridge have air conditioning?

Do house rentals in Woodbridge have free parking?

Are there vacation rentals with a dedicated workspace in Woodbridge?

Where should I stay in Woodbridge?

Destinations to explore