Photo by Darrell Bumbala

Woodmont Holiday Rentals

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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, (115)
"Spectacular views from the second floor balcony! very clean and spacious! Highly recommend staying here. "
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, (1966)
"Convenient location, helpful staff, comfortable bed. Thanks!"
The price is AU$175
includes taxes & fees
2 Dec - 3 Dec
New Haven Village Suites

Beachfront Romance: Rustic Home w/ Private Beach

9.2 out of 10, Wonderful, (46)
"We were looking for a small and private beach house getaway for the weekend and found this hidden gem. Our property manager, Debbie, made herself available throughout our stay to answer all of our questions. Everything needed for our comfort weekend was provided. We strongly recommend this place for those who are looking to get away from the hustle and bustle of city life. We will be returning! "
Beachfront Romance: Rustic Home w/ Private Beach

Business or Weekend escape

9.6 out of 10, Exceptional, (30)
"Stayed for my other half bday. Place was clean and described well"
The price is AU$154
includes taxes & fees
27 Nov - 28 Nov
Business or Weekend escape

DUNE Fairfield Beach

3.0 star property
8.8 out of 10, Excellent, (42)
"Beautiful and convenient location in a pretty neighborhood. Fairlt quiet on the 3rd floor, although some late night noise from party-ers but that was made clear on the website. Walkable to town and beach. Very comfortable stay! Thank you!"
The price is AU$446
includes taxes & fees
1 Dec - 2 Dec
DUNE Fairfield Beach

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

10.0 out of 10, Exceptional, (126)
"We stayed here for an anniversary weekend away and found the property and neighborhood to be amazing. We enjoyed the hot tub, pool and firepit and went kayaking in the afternoon. Enjoyed amazing sunsets from the deck; Adam gave us spot-on restaurant recommendations. I don't know if the supply of snacks is standard or an anniversary "special", but all in all this place was a wonderful find. Thank you!!"
Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub

Luxury Furnished Apartments by Hyatus Downtown at Yale

3.5 star property
9.8 out of 10, Exceptional, (34)
"Great location! Clean building And modern. "
Luxury Furnished Apartments by Hyatus Downtown at Yale

Beach Apt. Wineries, Shopping, Dining

5.2 out of 10, (7)
"The property manager ensured that booking and check in went smoothly. If you're looking for a 5 star resort or party house, this is NOT the location for you. However, if you're looking for a peaceful getaway on the north shore of Long Island, within walking distance to the beach with your small family, including pet, check it out. Is it flawless? well, no. But you'll find flaws where you look for them. The better question in my mind would be "would I opt to stay there again?".. and the answer is...
The price is AU$419
includes taxes & fees
30 Nov - 1 Dec
Beach Apt. Wineries, Shopping, Dining

Luxury Designer 2 bedroom+office/3bed vacation home.

9.4 out of 10, Exceptional, (15)
"Great little spot. Central enough to get everywhere we needed to. Walked to restaurants and to a concert (about 30 minutes). Host had some treats for us when we checked in. Apartment was clean and spacious. Felt comfortable walking around the neighborhood "
The price is AU$651
includes taxes & fees
1 Dec - 2 Dec
Luxury Designer 2 bedroom+office/3bed vacation home.

Westport Paradise With Every Amenity!

10.0 out of 10, Exceptional, (23)
"We had such a nice stay at Mark and Sarah’s. Check in was so easy and they were very attentive to anything we needed. The property and apartment are beautiful, it was so nice waking up and seeing all the trees and it was so quiet. We will definitely be back and stay when we are visiting our daughter at Fairfield."
The price is AU$1,109
includes taxes & fees
1 Dec - 2 Dec
Westport Paradise With Every Amenity!

BREATHTAKING BUNGALOW-HOME AWAY FROM HOME

10.0 out of 10, Exceptional, (25)
"The house was clean, and very comfortable. They are well stocked, even with our odd allergies, we were able to find some snacks. It saved us a good amount of town since it was a short visit. "
BREATHTAKING BUNGALOW-HOME AWAY FROM HOME

Soundview Beach House: 4BR,Panoramic Views 1.5hrsNYC, Sits Directly on beach

9.8 out of 10, Exceptional, (64)
"The house was exactly as advertised, the water views were beautiful! Easy access to the North Fork of Long Island."
Soundview Beach House: 4BR,Panoramic Views 1.5hrsNYC, Sits Directly on beach

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

10.0 out of 10, Exceptional, (58)
"Great"
Gorgeous Victorian direct ocean front single family six bedroom, ten rooms

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

10.0 out of 10, Exceptional, (23)
"This was a great spot to stay with friends, with great separate living areas and a great central living room to gather. The location is minutes from downtown Guilford and was very convenient to do and see everything. I would not recommend bringing small children because there is so much beautiful artwork all around the house, but it’s a beautiful retreat for older kids/teens and adults! "
A TREETOPS Retreat! Sleeps 10-12, perfect for large gatherings. Seasonal POOL!

(HIGH DEMAND)Close To Downtown Free Wi-fi/Parking/ Metro North & I-95 3 mins

8.6 out of 10, Excellent, (4)
"The location of Ms. Jay's place is unbeatable! My group and I were in town for an event in the Total Mortgage Arena. The drive was 5 minutes max! Ms. Jay is great with communication. She was always available for any questions. The apartment is very homey, cozy and comfortable. Very nicely decorated and it has everything you might need. (We would just recommend some mirrors in the bedrooms). The place is next to a very busy street which there is always a lot of noise, especially at night. One...
(HIGH DEMAND)Close To Downtown Free Wi-fi/Parking/ Metro North & I-95 3 mins

Waterfront Cottage in Branford

10.0 out of 10, Exceptional, (87)
"The house was perfect for our annual getaway. We are a group of nine women who have been friends for over 45 years. The large well stocked kitchen with amazing view of the water and fireplace made our Friendsgiving meal memorable! The outdoor hot tub, fire pit, and deck with comfy seating topped off the weekend. Great location, plenty of parking, responsive host. 5/5 stars! "
Waterfront Cottage in Branford

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

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

Coastal Retreat: Charming 3-Bedroom Fairfield Townhouse nr Beaches & Town Center

9.8 out of 10, Exceptional, (17)
"This place was super clean and exactly as described. "
Coastal Retreat: Charming 3-Bedroom Fairfield Townhouse nr Beaches & Town Center

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.

Cheerful 4 bedrooms residential house.

9.8 out of 10, Exceptional, (23)
"Washer downstairs unavailable, thermostat only on request, feather pillows (allergy). Otherwise it was ok with plenty of bedrooms and baths. "
Cheerful 4 bedrooms residential house.
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

New Haven Hotel

3.5 star property
8.8 out of 10, Excellent, (1398)
"The staff friendly and helpful . Room was comfortable,quiet and clean ."
The price is AU$228
includes taxes & fees
20 Dec - 21 Dec
New Haven Hotel

Motel 6 New Haven - Branford, CT

2.0 star property
6.6 out of 10, (1075)
"Thanks "
The price is AU$124
includes taxes & fees
1 Dec - 2 Dec
Motel 6 New Haven - Branford, CT

The Circle Hotel Fairfield

3.0 star property
8.8 out of 10, Excellent, (1253)
"Immaculately clean and comfortable beds . Cheerful decor. Safe and convenient location for restaurants and train services. Very pleasant staff . Would definitely stay again "
The price is AU$239
includes taxes & fees
1 Dec - 2 Dec
The Circle Hotel Fairfield
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.
Beautiful view of the beach with palm trees

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Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.

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?

Business or Weekend escape: This holiday home rental outside of Woodmont is equipped with a BBQ, air conditioning and a Smart TV to help you feel comfortable during your stay. Kitchen amenities include a fridge, a microwave and a coffee maker.

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 SportsCenter of Connecticut, 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.