Seymour Holiday Rentals

    calendar shield illustration
    Change your mind
    Book hotels with free cancellation
    deals illustration
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    bed illustration
    Be picky
    Search almost a million properties worldwide

Check prices for these dates

This weekend
Next weekend

Holiday Rentals in Seymour

DUNE Fairfield Beach

3.0 star property
9.0 out of 10, Wonderful, (59)
"Incredible staff, friendly, helpful. "
DUNE Fairfield Beach

Business or Weekend escape

9.2 out of 10, Wonderful, (40)
"Very nice owner with great communication. "
The price is NZ$241
includes taxes & fees
8 July - 9 July
Business or Weekend escape

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

10.0 out of 10, Exceptional, (131)
"My husband and I had a wonderful time at this idyllic cottage on the water in Branford. Great location and hosts. Beautiful community for long walks, restaurants nearby. Highly recommend! "
Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub

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

9.4 out of 10, Exceptional, (19)
"My stay was good only con was the parking. Parking was in the street and hope you come in early to get a space or you will park down the street… there is parking in the back for a fee which was not in the description of the property upon booking."
The price is NZ$676
includes taxes & fees
7 July - 8 July
Luxury Designer 2 bedroom+office/3bed vacation home.

Luxury Apartments by Hyatus at Pierpont

4.0 star property
9.4 out of 10, Exceptional, (18)
"Excellent location downtown and close to yale. A lot of complimentary amenities and activities. Very nice size rooms. A nice residential feel for a weeks stay."
Luxury Apartments by Hyatus at Pierpont

Charming Historic 2BR Retreat in New Haven – Cozy Stay Near Yale & Downtown!

10.0 out of 10, Exceptional, (5)
"We enjoyed our stay at this property. There was lots of room for us to gather and spend time together. The hosts were super helpful when we had any questions or issues and went out of their way to make our stay enjoyable. The property was close to Yale and the freeway, which made it easy to get around. The house was well appointed with everything we needed and was a great deal for the price. "
Charming Historic 2BR Retreat in New Haven – Cozy Stay Near Yale & Downtown!

Minutes to Walnut Beach, newly renovated 3 bedroom home

10.0 out of 10, Exceptional, (4)
"This house was perfect for our visit. It was clean and comfortable and provided everything we needed. Walking distance to a restaurant, coffee shop and the best ice cream! Would definitely stay here again. "
Minutes to Walnut Beach, newly renovated 3 bedroom home

Dog-Friendly Oceanfront Getaway - Walk to Dining - Private Beach Access

10.0 out of 10, Exceptional, (6)
"Property manager was very attentive to our needs and replied to all msgs in a very timely fashion. There were a couple things that needed tending to when we arrived and he took care of it immediately. Despite having parking on the street, it was never an issue and often got the spot that was right next to the house. The beach was directly across the street and was clean with friendly neighbors! Although there is a sign stating no dogs or animals allowed on the beach, there were many dogs on the...
The price is NZ$964
includes taxes & fees
22 July - 23 July
Dog-Friendly Oceanfront Getaway - Walk to Dining - Private Beach Access

Direct Waterfront Private Beach Escape

9.8 out of 10, Exceptional, (13)
"The house was great! Beautiful ocean front property with beachy vibes all throughout the neighborhood and interior of the home. The host was extremely clear on directions and provided amazing instructions. Very comfortable stay! "
Direct Waterfront Private Beach Escape

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

9.0 out of 10, Wonderful, (7)
"This property is well maintained. Some amenities available that made our stay more enjoyable. My only issue was the amount of noise you could hear throughout the night.but once you're asleep it doesn't matter. "
(HIGH DEMAND)Close To Downtown Free Wi-fi/Parking/ Metro North & I-95 3 mins

Relax by the River | Branford Waterfront Home

8.8 out of 10, Excellent, (3)
"Clean, family friendly, and fun."
Relax by the River | Branford Waterfront Home

Modern Courtland

2.0 out of 10, (1)
The price is NZ$628
includes taxes & fees
7 July - 8 July
Modern Courtland

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

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

The Daydreamer - Walk To Walnut Beach, Restaurant + Shops

9.8 out of 10, Exceptional, (9)
"5 Star stay!"
The Daydreamer - Walk To Walnut Beach, Restaurant + Shops

Main Street Westport, walk to shops, dining, downtown

8.0 out of 10, Very good, (1)
"It’s a good house - very basic - but gets job done - tricky driveway & noise from road is thing - we did not spend much time in house so was not much of factor Property managers were very helpful supportive"
Main Street Westport, walk to shops, dining, downtown

SALTY KISSES COZY BEACH HOUSE /BEACH ACCESS ACROSS STREET WATER VIEW

2.0 star property
10.0 out of 10, Exceptional, (3)
"The house was super cute, very clean and had a great location. Denise went above and beyond to make sure we had a lovey time. The backyard was beautiful and my kids loved all the critters and shells on the beach."
SALTY KISSES COZY BEACH HOUSE /BEACH ACCESS ACROSS STREET WATER VIEW

Cozy Cabin @ Sticks & Stones Farm

8.4 out of 10, Very good, (6)
"Nice clean cabin. Good communication with host."
Cozy Cabin @ Sticks & Stones Farm

Cozy 3 bedroom minutes from Yale and the beach

Cozy 3 bedroom minutes from Yale and the beach

Modern House in Black Rock

2.0 star property
9.0 out of 10, Wonderful, (6)
"Very easy stay and great location convenient to Fairfield University . Plenty of options to walk to for coffee or meals. Had everything we needed. Clean, well equipped. Great communication with owners. "
Modern House in Black Rock

Candlewood Lake Retreat

10.0 out of 10, Exceptional, (2)
"Excellent facilities at this great property. Really good outdoor deck, good sized bedrooms, huge tv next to the table football in the basement, really good kitchen facilities. The host Raymond was very helpful, and Uber happy to bring you home if need be."
Candlewood Lake Retreat
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.
Save an average of 15% on thousands of hotels when you're signed in

Frequently asked questions

Are there holiday rentals in Seymour?

Yes, there are holiday rentals in Seymour close to Waterski Connecticut, or you can select a more secluded option if you're looking for a relaxing stay. Seymour is known for its restaurants and shopping. Make sure you have time to check out the beaches while you're in the area.

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

Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub : This holiday home rental outside of Seymour is located on the beach, and has an outdoor pool, a balcony and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave. Kick off your shoes and enjoy yourself with a garden and 1 hot tub.

How many holiday rentals will I find in Seymour?

Choose from 3 Expedia holiday rentals in Seymour for a memorable holiday.

What can I see and do in Seymour?

Family-friendly attractions include Waterski Connecticut, whereas Housatonic River is a spot to enjoy the outdoors. In the wider area, you’ll find Indian Well State Park and Yale Golf Course.

What are holiday rentals like in Seymour?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Seymour. Holiday rentals feature extras like WiFi and washers and dryers so you'll be comfy for your stay. If you're concerned about a clean environment, holiday rentals can provide a sense of security away from public hotel lifts and busy lobbies while still allowing you to travel. You'll also get more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a popular option for a small group gathering.