Book Holiday Homes in Woodbury

More Flash, Less Cash - Take advantage of our Price Pledge** (even on luxey stays)

We keep it easy with the option to pay now or later on select accommodation

Book up 'til the last second - millions of rooms to crash tonight^

Featured Holiday Homes in Woodbury

Beautiful Renovated Direct Waterfront Candlewood Lake Home~Views~Weekly Discount

Beautiful Renovated Direct Waterfront Candlewood Lake Home~Views~Weekly Discount

Danbury CT
Located in Danbury, this vacation home is on the waterfront, a 2-minute drive from Candlewood Lake and 7 minutes from Candlewood Plaza Shopping Center.
Opens in a new windowBeautiful Renovated Direct Waterfront Candlewood Lake Home~Views~Weekly Discount
Stylish & Luxurious 3 BDR Home with Play Station

Stylish & Luxurious 3 BDR Home with Play Station

Bristol CT
With a stay at this vacation home in Bristol, you'll be within a 5-minute drive of Bristol Commons Shopping Center and Wilson Playground.
Opens in a new windowStylish & Luxurious 3 BDR Home with Play Station
Cozy Lakefront Bungalow w firepit/dock/kayaks

Cozy Lakefront Bungalow w firepit/dock/kayaks

Plymouth CT
Located in Plymouth, this vacation home is on the waterfront, within a 15-minute drive of Black Rock State Park and Rockwell Park.
Opens in a new windowCozy Lakefront Bungalow w firepit/dock/kayaks
Save an average of 15% on thousands of hotels when you're signed in
Nature's Nest - Indoor/Outdoor Forest Retreat; Fire Pit; Fireplace; onsite Brook

Nature's Nest - Indoor/Outdoor Forest Retreat; Fire Pit; Fireplace; onsite Brook

Bethlehem CT
With a stay at this vacation home in Bethlehem, you'll be within a 5-minute drive of The Christmas Shop and Little Art Shop.
Opens in a new windowNature's Nest - Indoor/Outdoor Forest Retreat; Fire Pit; Fireplace; onsite Brook
Escape to a Luxury Lakehouse Retreat- Chefs Indoor Outdoor Kitchen Hot Tub Steam

Escape to a Luxury Lakehouse Retreat- Chefs Indoor Outdoor Kitchen Hot Tub Steam

New Fairfield CT
With a stay at this vacation home in New Fairfield, you'll be on the waterfront, just steps from Candlewood Lake and a 3-minute drive from Squantz Pond State ...
Opens in a new windowEscape to a Luxury Lakehouse Retreat- Chefs Indoor Outdoor Kitchen Hot Tub Steam
Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville

Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville

Collinsville CT
The price is AU$743 per night from 26 May to 27 May
AU$743
26 May - 27 May
includes taxes & fees
With a stay at this vacation home in Canton (Collinsville), you'll be steps from Farmington River and a 3-minute drive from Canton Green Shopping Center.
Opens in a new windowGorgeous River Views! On Rails to Trails and just steps to quaint Collinsville
Modern cozy home, pet friendly

Modern cozy home, pet friendly

Wolcott CT
Located in Wolcott, this vacation home is within a 15-minute drive of Peterson Park and Mattatuck Beach.
Opens in a new windowModern cozy home, pet friendly
Lake house cozy to relax with a family. 6 bedroom very spacious house.

Lake house cozy to relax with a family. 6 bedroom very spacious house.

Trumbull CT
With a stay at this vacation home in Trumbull, you'll be within a 15-minute drive of Hartford HealthCare Amphitheater and Monroe Plaza Shopping Center.
Opens in a new windowLake house cozy to relax with a family. 6 bedroom very spacious house.
Relaxing Lake House Retreat Family Friendly

Relaxing Lake House Retreat Family Friendly

Wolcott CT
Located in Wolcott, this vacation home is a 4-minute drive from Mattatuck Beach and 5 minutes from Mount Southington Ski Area.
Opens in a new windowRelaxing Lake House Retreat Family Friendly
Don't see what you're looking for?
See all available properties in Woodbury
View all properties
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.

Woodbury Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Woodbury vacation homes are the perfect way for you to wing it.

Holiday houses in Woodbury let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Woodbury in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Woodbury adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Woodbury with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Woodbury vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Woodbury Holiday Homes essential information

Accommodation
269 Holiday Homes
Lowest Price
AU$140
Highest Price
AU$743
Popular accommodation
Beautiful Renovated Direct Waterfront Candlewood Lake Home~Views~Weekly Discount, Stylish & Luxurious 3 BDR Home with Play Station, Cozy Lakefront Bungalow w firepit/dock/kayaks, Nature's Nest - Indoor/Outdoor Forest Retreat; Fire Pit; Fireplace; onsite Brook, Escape to a Luxury Lakehouse Retreat- Chefs Indoor Outdoor Kitchen Hot Tub Steam, Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville, Modern cozy home, pet friendly, Lake house cozy to relax with a family. 6 bedroom very spacious house., Relaxing Lake House Retreat Family Friendly

Top trending hotels in Woodbury

Holiday Inn Express Southington by IHG

Holiday Inn Express Southington by IHG

2.5 out of 5
120 Laning St Southington CT
Fully refundableReserve now, pay when you stay
The price is AU$167 per night from 25 May to 26 May
AU$167
25 May - 26 May
includes taxes & fees
Located in Southington, Holiday Inn Express Southington by IHG is in the business district, within a 10-minute drive of Hawks Landing Country Club and New Britain ...
Opens in a new windowHoliday Inn Express Southington by IHG
Hilton Garden Inn Shelton

Hilton Garden Inn Shelton

3 out of 5
25 Old Stratford Rd Shelton CT
Fully refundableReserve now, pay when you stay
The price is AU$170 per night from 24 May to 25 May
AU$170
24 May - 25 May
includes taxes & fees
With a stay at Hilton Garden Inn Shelton in Shelton, you'll be in the business district, within a 15-minute drive of Hartford HealthCare Amphitheater and Shelton ...
Opens in a new windowHilton Garden Inn Shelton
Courtyard by Marriott Waterbury Downtown

Courtyard by Marriott Waterbury Downtown

3 out of 5
63 Grand St Waterbury CT
Fully refundableReserve now, pay when you stay
The price is AU$143 per night from 26 May to 27 May
AU$143
26 May - 27 May
includes taxes & fees
A stay at Courtyard by Marriott Waterbury Downtown places you in the heart of Waterbury, within a 5-minute walk of Waterbury City Hall and Apothecary ...
Opens in a new windowCourtyard by Marriott Waterbury Downtown
Save an average of 15% on thousands of hotels when you're signed in
Best Western Danbury/Bethel

Best Western Danbury/Bethel

2.5 out of 5
11 Stony Hill Road Bethel CT
Fully refundableReserve now, pay when you stay
The price is AU$140 per night from 24 May to 25 May
AU$140
24 May - 25 May
includes taxes & fees
With a stay at Best Western Danbury/Bethel in Bethel, you'll be near the airport, just steps from The Cave and a 2-minute drive from Still River Greenway.
Opens in a new windowBest Western Danbury/Bethel
Don't see what you're looking for?
See all available properties in Woodbury
View all properties
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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.