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, (105)
"We had an absolutely fantastic long weekend at this spacious and beautiful house near the beach! It was a perfect getaway for our extended family, with ample room for everyone to spread out comfortably. We enjoyed leisurely walks by the beach, cozy evenings gathered around the fireplace, and breathtaking views that truly enhanced our stay. The house was impeccably clean and well-maintained, exactly as advertised. We couldn't have asked for a better retreat. Highly recommended for anyone looking...
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, (1857)
"We stayed only one night as planned. The property is in need of renovation, more than just paint. Our room had a musty smell and the carpets were worn out. The people working there were great. I hope they can rejuvenate this area. "
The price is NZ$177
includes taxes & fees
7 July - 8 July
New Haven Village Suites
Beachfront Romance: Rustic Home w/ Private Beach
9.2 out of 10, Wonderful, (41)
"Love this place! Nice beach and quiet road. Great restaurant 5 minutes away."
Beachfront Romance: Rustic Home w/ Private Beach
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Business or Weekend escape
9.6 out of 10, Exceptional, (18)
"Mansoor's place has many amenities to make your stay as comfortable as possible. We appreciated the quiet street, comfortable bed, dining space, fridge with drinks and bathroom with all necessities. Thanks, Mansoor for another great stay."
The price is NZ$222
includes taxes & fees
30 June - 1 July
Business or Weekend escape
DUNE Fairfield Beach
3.0 star property
8.8 out of 10, Excellent, (14)
"perfectly clean, quiet, great location "
The price is NZ$475
includes taxes & fees
1 July - 2 July
DUNE Fairfield Beach
Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub
10.0 out of 10, Exceptional, (113)
"Was looking for a coastal retreat to enjoy a couple days with my daughter who lives near this location. This property had everything from a super clean, cozy studio with fridge and counters filled with surprising treats, incredible hot tub with lights in the trees, pool to cool off and little private beach to launch a paddlleboard and kayak, or hang out at night with a burn pit. If you are just a beach person and want toes in the sand and to swim in the ocean, this area is not for you....
Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub
Luxury Designer 2 bedroom+office/3bed vacation home.
9.2 out of 10, Wonderful, (12)
"This was a great place. Very clean. Much larger than the photos make it seem. Host was very responsive. Neighborhood was a bit sketchy but overall a very comfortable and nice stay. Very close to the Hartford Healthcare Amphitheater which is where we needed to go. Would definitely return and highly recommend!"
The price is NZ$715
includes taxes & fees
10 July - 11 July
Luxury Designer 2 bedroom+office/3bed vacation home.
Beach Apt. Wineries, Shopping, Dining
6.8 out of 10, (3)
"The property manager was great! Place was very nice even though we were really only there to sleep. Will definitely consider in the future!"
The price is NZ$494
includes taxes & fees
15 July - 16 July
Beach Apt. Wineries, Shopping, Dining
Westport Paradise With Every Amenity!
10.0 out of 10, Exceptional, (14)
"The guest house was spacious and well appointed. The furnishings were very comfortable. The grounds at the house are beautiful. We thoroughly enjoyed our stay."
The price is NZ$1,592
includes taxes & fees
2 July - 3 July
Westport Paradise With Every Amenity!
Cozy, fully remodeled water view home on quiet cul de sac
9.8 out of 10, Exceptional, (100)
"My family and I needed a home base when visiting with a sick member and Cheri's place was perfect. Clean, quiet, spacious and comfortable. Would highly recommend!"
Cozy, fully remodeled water view home on quiet cul de sac
Luxury Furnished Apartments by Hyatus Downtown at Yale
3.5 star property
10.0 out of 10, Exceptional, (24)
"This was an amazing property to stay at. Super accommodating when we needed to extend our stay. Very clean and easy to check in and out of. They thought of everything even down to the toothpaste!"
Luxury Furnished Apartments by Hyatus Downtown at Yale
BREATHTAKING BUNGALOW-HOME AWAY FROM HOME
10.0 out of 10, Exceptional, (16)
"We chose this cottage again because we liked it so much last year. It works very well for the two of us, and the owner goes above and beyond to make sure we are comfortable."
BREATHTAKING BUNGALOW-HOME AWAY FROM HOME
Soundview Beach House: 4BR,Panoramic Views 1.5hrsNYC, Sits Directly on beach
9.8 out of 10, Exceptional, (53)
"We enjoyed our stay specially the sunsets. The house had everything we needed to make us feel at home."
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, (52)
"We had a wonderful weekend. The house was perfect and completely met all our needs. Great location and views."
gorgeous victorian direct ocean front single family six bedroom, ten rooms
(HIGH DEMAND)Close To Downtown Free Wi-fi/Parking/ Metro North & I-95 3 mins
9.4 out of 10, Exceptional, (3)
"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
Grace Island. Private Island! Vacations, Getaways, Weddings & Special Events.
Grace Island. Private Island! Vacations, Getaways, Weddings & Special Events.
Waterfront Cottage in Branford
10.0 out of 10, Exceptional, (81)
"Beautiful house in a beautiful location! We hope to return soon!"
Waterfront Cottage in Branford
Direct Beachfront Property On Long Island Sound
10.0 out of 10, Exceptional, (26)
"We had a wonderful time on the beach, in the ocean and just relaxing in the house. There were nice restaurants in the area to try and some fun day trips to take with the kids. We'd go back!"
Direct Beachfront Property On Long Island Sound
The Dream Location for Your Perfect Vacation
9.8 out of 10, Exceptional, (15)
"The cottage has the most wonderful views! We loved our stay!"
The Dream Location for Your Perfect Vacation
Coastal Retreat: Charming 3-Bedroom Fairfield Townhouse nr Beaches & Town Center
10.0 out of 10, Exceptional, (12)
"Stayed at Coastal Retreat for a weekend visit with son who attends Fairfield University, brought both sets of parents and teen daughter (ages ranging 73-16), plenty of room and able to enjoy a wonderful family dinner with son even in attendance. Wonderful area, close walk to beach and easy to get to downtown Fairfield and university. Very clean and welcoming! Greg was wonderful to work with and answered any question we had that came up both prior and upon arrival. The only thing we would mention...
Coastal Retreat: Charming 3-Bedroom Fairfield Townhouse nr Beaches & Town Center
Don't see what you're looking for?
See all available properties in Woodmont
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.

Other types of properties in Woodmont you may be interested in

New Haven Hotel
3.5 star property
8.8 out of 10, Excellent, (1265)
"Good location for short visits. Room was nice. "
The price is NZ$281
includes taxes & fees
21 July - 22 July
New Haven Hotel
The Circle Hotel Fairfield
3.0 star property
8.8 out of 10, Excellent, (1145)
"The Circle Motel was clean and had very comfortable beds. It is a classic, vintage motel which makes it fun. "
The price is NZ$296
includes taxes & fees
8 July - 9 July
The Circle Hotel Fairfield
Cambria Hotel New Haven University Area
3.0 star property
8.8 out of 10, Excellent, (390)
"Staff was incredibly friendly, the hotel was incredibly clean, the restaurant was really good. Will stay there again next year."
The price is NZ$255
includes taxes & fees
21 July - 22 July
Cambria Hotel New Haven University Area
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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Woodmont holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Woodmont. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Woodmont. Seeing all the best attractions is bound to make you fall in love with Woodmont. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Woodmont short-term rentals, that won’t be hard to do.

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 has air conditioning and WiFi to help you feel perfectly comfortable in your new surroundings.

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 Seabluff Beach. In the wider area, you’ll find Westfield Connecticut Post Mall and Sandy Point Beach.

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.

Recent reviews of Woodmont properties
Expedia verified reviews