Photo by Darrell Bumbala

Holiday Rentals in Woodmont

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Holiday Rentals in Woodmont

Beach Front Arts & Crafts House With Gorgeous Views Of The Sound

10.0 out of 10, Exceptional, (116)
"The Arts and Crafts home was more beautiful than the pictures reflected! We loved all of the details in the woodwork, hidden little corners, tons of space to spread out and wonderful places to gather together. Having recently sold our "family home" we were thrilled to find this home in which to have a mini- family reunion. The kitchen was incredibly well-stocked- from serving platters to garlic powder to paper towels...We had everything we needed. The gas fireplace created a beautiful focal...
Beach Front Arts & Crafts House With Gorgeous Views Of The Sound

New Haven Village Suites

3.0 star property
7.6 out of 10, Good, (2005)
"Easy fast check in"
The price is €97
includes taxes & fees
3 Mar - 4 Mar
New Haven Village Suites

DUNE Fairfield Beach

3.0 star property
8.8 out of 10, Excellent, (46)
"My daughter and I stayed 2 nights while visiting colleges in the area. The room was cute (modern, beach-vibe) and clean. As others mentioned when the bar let out around midnight it was a little loud (many college students rent in the area). I also didn’t care for the mini-split going on and off throughout the night - I’m just not used to that noise. Overall it was a fine stay but perhaps not if you are a light-sleeper. "
The price is €305
includes taxes & fees
24 Feb - 25 Feb
DUNE Fairfield Beach

Luxury Furnished Apartments by Hyatus Downtown at Yale

3.5 star property
9.8 out of 10, Exceptional, (38)
"Great location. Nice place. Noisy neighbors though"
Luxury Furnished Apartments by Hyatus Downtown at Yale

Grace Island. Private Island! Vacations, Getaways, Weddings & Special Events.

Grace Island. Private Island! Vacations, Getaways, Weddings & Special Events.

Business or Weekend escape

9.6 out of 10, Exceptional, (31)
"Great location right around the corner from everything. Comfy and clean furniture great sense of humor with decorations on the wall overall great experience 10/10 will definitely rebook"
The price is €134
includes taxes & fees
23 Feb - 24 Feb
Business or Weekend escape

Gorgeous Victorian direct ocean front single family six bedroom, ten rooms

10.0 out of 10, Exceptional, (59)
"Our family ranged in ages from 13 to 96. We were 12 people for a couple days and then 10. We all had a marvelous time and my mom just can’t stop talking about how beautiful the view and the antique furniture was. It was difficult for that many people only having two bathrooms, but we made it work. We did run out of hot water so we learned to scatter showers when possible. The view is amazing and the location was wonderful for us. I can’t say enough, how accommodating our hostess was. We told her...
Gorgeous Victorian direct ocean front single family six bedroom, ten rooms

Cozy Country Cottage #3

10.0 out of 10, Exceptional, (14)
"Very clean and comfortable "
The price is €277
includes taxes & fees
5 Mar - 6 Mar
Cozy Country Cottage #3

A TREETOPS Retreat! Sleeps 10-12, perfect for large gatherings. Seasonal POOL!

10.0 out of 10, Exceptional, (24)
"The house is an architectural gem with plenty of space for the family. We enjoyed the fireplace in the evenings."
A TREETOPS Retreat! Sleeps 10-12, perfect for large gatherings. Seasonal POOL!

Beach Apt. Wineries, Shopping, Dining

6.2 out of 10, (10)
"It was a decent place to stay."
The price is €218
includes taxes & fees
21 Feb - 22 Feb
Beach Apt. Wineries, Shopping, Dining

BREATHTAKING BUNGALOW-HOME AWAY FROM HOME

10.0 out of 10, Exceptional, (27)
"Wonderful little bungalow. Owners are really nice and responsive. House is well maintained, cleaned and better stocked than any other rental we've been in. Thank you!!"
BREATHTAKING BUNGALOW-HOME AWAY FROM HOME

Cozy Cabin @ Sticks & Stones Farm

8.0 out of 10, Very good, (2)
"If you pictured this property minutes from the historic district of Newtown it’s exactly that. The space brings to life the feeling of the rustic yet comfortable aspect of Connecticut. My adult son and teenage daughter were comfortable but thoroughly enjoyed the living room fireplace. This location is 10 minutes away from restaurants that will please most families with a mix of family to high end with a side of fancy. "
The price is €186
includes taxes & fees
9 Mar - 10 Mar
Cozy Cabin @ Sticks & Stones Farm

New Madison beach house - Ocean front- Great views- booking Summer 2025

10.0 out of 10, Exceptional, (56)
"Great location "
New Madison beach house - Ocean front- Great views- booking Summer 2025

Beautiful 4BR Beach House with Private Beach Access.

9.8 out of 10, Exceptional, (69)
"our annual girls (5) trip took us to Branford, CT this year. It was awesome to have a private beach access even though we couldn’t get in the water, but it was great for strolls and shell collecting. Would definitely do better with a second bathroom, but we managed just fine. Overall, it’s a nice little place to stay for a getaway. My only issue is not with the hosts or place, but with one of the fees and the checkout process. However, it does not take away from our stay. "
Beautiful 4BR Beach House with Private Beach Access.

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

10.0 out of 10, Exceptional, (128)
"having previously rented VRBO properties in Palm Springs, West Palm Beach & Ft. Lauderdale I can confirm this property is exceptional. The studio has 1st tier amenities, waterfront location & in addition the hosts provided most welcoming foods and snacks, an overall wonderful experienceJimBrooklyn, NY"
Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub

Luxury Apartments by Hyatus at Pierpont

4.0 star property
9.4 out of 10, Exceptional, (13)
"Great. Would prefer to anyone"
Luxury Apartments by Hyatus at Pierpont

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.

Beautiful, Spacious, Beachfront Home - Perfect for Entertaining Family & Friends

10.0 out of 10, Exceptional, (46)
"The house was beautiful and a perfect place for our family to be at while visiting our daughter who is a student at Yale. We saw the sunrise over the ocean from our bedroom window. Wish we found this sooner!"
Beautiful, Spacious, Beachfront Home - Perfect for Entertaining Family & Friends

Cheerful 4 bedrooms residential house.

9.8 out of 10, Exceptional, (26)
"The house was clean, comfortable, and kitchen was great. Only problem was stairs for my handicapped sister-too steep but possible. Manager very nice"
Cheerful 4 bedrooms residential house.

Ocean Front Beach House with Private Beach Access - Newly Renovated!

10.0 out of 10, Exceptional, (13)
"Wonderful week at this beautiful home! Great space, comfortable furniture, well equipped. Breathtaking sunrises AND sunsets. Highly recommend this home !"
Ocean Front Beach House with Private Beach Access - Newly Renovated!
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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Other types of properties in Woodmont you may be interested in

Beach Front Arts & Crafts House With Gorgeous Views Of The Sound

10.0 out of 10, Exceptional, (116)
"The Arts and Crafts home was more beautiful than the pictures reflected! We loved all of the details in the woodwork, hidden little corners, tons of space to spread out and wonderful places to gather together. Having recently sold our "family home" we were thrilled to find this home in which to have a mini- family reunion. The kitchen was incredibly well-stocked- from serving platters to garlic powder to paper towels...We had everything we needed. The gas fireplace created a beautiful focal...
Beach Front Arts & Crafts House With Gorgeous Views Of The Sound

New Haven Hotel

3.5 star property
8.8 out of 10, Excellent, (1462)
"Kudos to Rachel at the front desk in the evening of 1/17 (who helped fix the lack of hot water in our sink/shower), and Stephanie and Luis Reyes on the early morning of 1/19. Stephanie and Luis were instrumental in helping me with jump my car's dead battery. Stephanie got a hold of Luis, and Luis went to the gararge to jump the battery. They saved our day! Bravo to the fine staff at the New Haven Hotel. With much gratitude, Doug and Lisa"
The price is €130
includes taxes & fees
23 Mar - 24 Mar
New Haven Hotel

Omni New Haven Hotel at Yale

4.0 star property
8.2 out of 10, Very good, (1003)
"Nice property and room."
The price is €166
includes taxes & fees
5 Mar - 6 Mar
Omni New Haven Hotel at Yale
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.

Frequently asked questions

Can I find holiday rentals in Woodmont?

Yes, there are holiday rentals close to the most popular sights in Woodmont, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Woodmont has to offer?

Beach Front Arts & Crafts House With Gorgeous Views Of The Sound: This highly rated holiday home rental in Woodmont is located on the beach, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 6 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

How many holiday rentals will I find in Woodmont?

Choose from 6 Expedia holiday rentals in Woodmont for a memorable holiday.

What’s there to see and do in Woodmont?

While exploring the area, visit family-friendly sights like Peabody Museum of Natural History, or get outside and enjoy nature at Sandy Point Beach. In the wider area, you’ll find Westfield Connecticut Post Mall and Milford Green.

What’s a holiday rental in Woodmont like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Woodmont. Holiday rentals provide amenities such as hot tubs, fire pits and patios so you'll have all the conveniences of home. If you're concerned about cleanliness, holiday rentals can offer a sense of safety away from public hotel lifts and lobbies bustling with people while still allowing you the experience of travel. You'll also get more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is an attractive choice for a family getaway.