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

In two weeks
In one month
In two months
In three months

Holiday Rentals in Seymour

DUNE Fairfield Beach

3.0 star property
9.0 out of 10, Wonderful, (67)
"Incredible staff, friendly, helpful. "
DUNE Fairfield Beach

Business or Weekend escape

9.2 out of 10, Wonderful, (45)
"We had stayed at Mansoor's a few weeks ago and returned this past weekend. Once again, we found the place spotless, comfortable and well-stocked. We really like this place and expect to return again in the future. "
The price is HK$662
HK$1,141 total
includes taxes & fees
14 Sept - 15 Sept
Business or Weekend escape

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

10.0 out of 10, Exceptional, (141)
"Perfect location for a get-away! Beautiful location on the water. The cottage was cozy & had everything we needed. Very clean. Lots to do in the area. Host was very nice We had a great time and will absolutely be back! "
Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub

Lakeside/Sleeps20/HotTub/GameRoom/2Acres/Firepit

10.0 out of 10, Exceptional, (1)
Lakeside/Sleeps20/HotTub/GameRoom/2Acres/Firepit

Luxury Furnished Apartments by Hyatus Downtown at Yale

3.5 star property
9.6 out of 10, Exceptional, (54)
"Loved the property and we will surely be coming back."
Luxury Furnished Apartments by Hyatus Downtown at Yale

Modern Beach Home - Waterview, close to restaurants, universities and hospitals

10.0 out of 10, Exceptional, (1)
"The check in process was very easy. The home was airy and bright. My family and I felt the peace and relaxation of the home. The kitchen was large and clean."
Modern Beach Home - Waterview, close to restaurants, universities and hospitals

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

10.0 out of 10, Exceptional, (124)
"The house is beautiful, and one of the most unique and homey places we have everything stayed. Very spacious with lots of artwork, and arts and crafts style woodwork. The view of the sound is so serene. We enjoyed very much sitting out on the porch and gazing at the water and the passerbys, and taking walks along the sound. It has everything you need and then some. Thank you so much for sharing your gracious and beautiful home with us!"
Beach Front Arts & Crafts House With Gorgeous Views Of The Sound

Exclusive Weekend Summer Sale here Waterfront Beach Home🏖️Hot Tub+Stunning Views

9.8 out of 10, Exceptional, (66)
"We very much enjoyed our stay and were pleasantly surprised by how great the views were from practically every room in the house. Check-in was very simple and there were many nice touches awaiting us at the property. "
Exclusive Weekend Summer Sale here Waterfront Beach Home🏖️Hot Tub+Stunning Views

Seven Sleeps + Patio retreat/lake + Two-in-one game table/PS5

10.0 out of 10, Exceptional, (1)
"This place was very clean and Michael was great, answering all my questions quickly. check in was simple just a code to get in it was very updated and the beds were very comfortable. It was close to Yale and to some great pizza places"
Seven Sleeps + Patio retreat/lake + Two-in-one game table/PS5

Charming Colonial for Events and Getaways! – Perfect for Family Retreat!

10.0 out of 10, Exceptional, (2)
"This property is absolutely beautiful. Extremely clean. The host was very attentive to my questions before and after check in. The host checked on my family during our stay. The yard, the porches, and the entire interior are so cozy and comfortable. The check in and check out processes were smooth. The neighborhood is quiet. I am already looking forward to going back! Definitely recommend the Beechmont House"
The price is HK$5,607
HK$10,765 total
includes taxes & fees
30 Aug - 31 Aug
Charming Colonial for Events and Getaways! – Perfect for Family Retreat!

Cozy Home Near New Haven

10.0 out of 10, Exceptional, (1)
"So comfy for the dog and I for a night. Just what we needed!"
The price is HK$939
HK$1,236 total
includes taxes & fees
9 Sept - 10 Sept
Cozy Home Near New Haven

Candlewood Lakefront 3bd/ 2 bath house w/ 180 degree views!

10.0 out of 10, Exceptional, (45)
"Wonderful property with a great location."
Candlewood Lakefront 3bd/ 2 bath house w/ 180 degree views!

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

9.4 out of 10, Exceptional, (20)
"Had a great stay!"
The price is HK$1,152
HK$3,264 total
includes taxes & fees
1 Sept - 2 Sept
Luxury Designer 2 bedroom+office/3bed vacation home.

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

Lovely Bohemian Loft Downtwn, Amphitheater,Seaside Park,Metro North,2-10min walk

10.0 out of 10, Exceptional, (2)
"Such a cute vibey apartment and the host was so nice and easy to talk to--would love to stay here again!"
The price is HK$1,090
HK$1,768 total
includes taxes & fees
1 Sept - 2 Sept
Lovely Bohemian Loft Downtwn, Amphitheater,Seaside Park,Metro North,2-10min walk

Direct Waterfront Private Beach Escape

9.6 out of 10, Exceptional, (18)
"Thank you so Much, the family had a great time. Found some good seaglass"
Direct Waterfront Private Beach Escape

Cheerful 4 bedrooms residential house.

9.8 out of 10, Exceptional, (33)
"House was very clean and maintained. We needed to check in a day later and the host was very accommodating. Overall a great place to stay! "
Cheerful 4 bedrooms residential house.

Adorable Beach Cottage

10.0 out of 10, Exceptional, (44)
"This property is perfect for two or 3 adults. Charming cottage, very clean, great beach community. "
Adorable Beach Cottage

Cozy 1-bedroom apartment in cool New Haven with WiFi, fitness room

The price is HK$1,191
HK$2,351 total
includes taxes & fees
30 Aug - 31 Aug
Cozy 1-bedroom apartment in cool New Haven with WiFi, fitness room

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

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

Top Seymour Hotel Reviews

Find out more about Seymour

Find out more about Seymour

Search for holiday rentals in Seymour on Expedia! You can easily find your home rentals, villas, holiday apartments in Seymour using one of the methods below:

  • View our selection of featured holiday rentals in Seymour
  • Use the map to find apartments and other holiday homes in the Seymour neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Seymour while they last

Look no further and take a look at our great range of rental properties in Seymour!

Explore a world of travel with Expedia

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?

Business or Weekend escape: This holiday home rental outside of Seymour 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.

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 Southern Connecticut State University.

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.