Vacation rentals in Woodbridge

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Woodbridge

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

Guest favorite

Apartment in Milford

4.97 out of 5 average rating, 505 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!

Aug 27 – Sep 3

G$42,008 GYD per night
Guest favorite

Guesthouse in Southbury

4.93 out of 5 average rating, 265 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 14 – 21

G$32,379 GYD per night
Guest favorite

Guest suite in Bethlehem

4.99 out of 5 average rating, 193 reviews

Breezy Crest private & restful w/antique charm

Escape to this charming and historic two-story 1841 suite, nestled in the quaint town of Bethlehem. The upstairs bedroom boasts original exposed beams and antique details, creating a cozy and inviting atmosphere. Wake up to the sunrise from the comfort of your bed and enjoy a warm fire in the backyard while listening to the peaceful sounds of nature. Conveniently located between Litchfield and Woodbury, and just 90 miles from NYC, you'll have easy access to shops, restaurants, and ski slopes.

Apr 20 – 27

G$22,803 GYD per night

Popular amenities for Woodbridge vacation rentals

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

Apartment in New Haven

4.93 out of 5 average rating, 190 reviews

Perfect for Yale and New Haven Visits

Oct 4 – 11

G$33,815 GYD per night
Guest favorite

Apartment in New Haven

4.99 out of 5 average rating, 103 reviews

Bright 1 BR Apt Steps From Yale

Sep 30 – Oct 7

G$33,141 GYD per night
Guest favorite

Home in North Haven

5.0 out of 5 average rating, 122 reviews

Luxury Stay in Expansive Historical Home

Jun 27 – Jul 4

G$171,274 GYD per night
Superhost

Apartment in West Haven

4.85 out of 5 average rating, 27 reviews

Beautiful New Studio Close to Yale!

May 28 – Jun 4

G$20,961 GYD per night
Guest favorite

Guest suite in New Haven

4.87 out of 5 average rating, 31 reviews

The West Rock “Tree-House”

Apr 16 – 23

G$24,906 GYD per night
Guest favorite

Home in Hamden

5.0 out of 5 average rating, 24 reviews

Entire Home in Hamden

Aug 27 – Sep 3

G$36,169 GYD per night
Guest favorite

Apartment in Milford

5.0 out of 5 average rating, 46 reviews

The Pond Mill Retreat w/ 2 Bdrms & Pool

Aug 7 – 14

G$33,616 GYD per night
Guest favorite

Apartment in New Haven

5.0 out of 5 average rating, 52 reviews

Retreat in New Haven by Stephanie and Damian

Aug 23 – 30

G$40,815 GYD per night
Superhost

Guesthouse in Branford

4.79 out of 5 average rating, 47 reviews

Studio on the shore - Short Beach - Water Views

Dec 7 – 14

G$21,213 GYD per night
Guest favorite

Apartment in Middlebury

4.98 out of 5 average rating, 61 reviews

Cozy Apartment with Water View of Brook

Aug 29 – Sep 5

G$21,428 GYD per night
Guest favorite

Home in Southbury

5.0 out of 5 average rating, 53 reviews

The Cottage at Cedar Spring Farm

Aug 6 – 13

G$33,614 GYD per night
Guest favorite

Cabin in Milford

5.0 out of 5 average rating, 12 reviews

Long Stays! Charming Coast Cabin| Near Beach| Pets

Apr 12 – 19

G$20,493 GYD per night

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 apartment rentals in Woodbridge have free parking?

    Absolutely! We offer over 10 apartment 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 1,050 vacation rentals in West New Haven, and over 980 vacation rentals in Westville.

Destinations to explore