Seymour Holiday Rentals

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Holiday Rentals in Seymour

DUNE Fairfield Beach

3.0 star property
Fairfield
9.0 out of 10, Wonderful, (76)
"Loved this venue! "
United States
adriano
DUNE Fairfield Beach

Luxury Furnished Apartments by Hyatus Downtown at Yale

3.5 star property
The Hill
9.6 out of 10, Exceptional, (60)
"Loved our stay here. "
United States
Christina
Luxury Furnished Apartments by Hyatus Downtown at Yale

Charming Colonial for Events! – Perfect for Family Reunions and Group Getaways!

North End
9.6 out of 10, Exceptional, (4)
"Very clean house. set up very nicely, landlord was very responsive and helpful. perfect for what we needed "
United States
Nancy H.
The price is NZ$2,443
includes taxes & fees
20 Nov - 21 Nov
Charming Colonial for Events! – Perfect for Family Reunions and Group Getaways!

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

Brookfield
9.6 out of 10, Exceptional, (4)
"The host was very kind and welcoming. The home was spacious and the perfect setting for our celebration weekend. Everyone had their own space and we had multiple spaces for group activities. We enjoyed our time and appreciate the hospitality. "
United States
Valerie V.
Lakeside/Sleeps20/HotTub/GameRoom/2Acres/Firepit

Business or Weekend escape

Stratford
9.2 out of 10, Wonderful, (51)
"Clean room, easy check-in, parking available on-site "
United States
Cindy
The price is NZ$249
includes taxes & fees
23 Nov - 24 Nov
Business or Weekend escape

Peaceful Vintage Home with Private Lake in Redding, CT.

2.0 star property
Redding
10.0 out of 10, Exceptional, (2)
"Several of us stayed for one night for our kids soccer tournament. The home was spacious and had all the amenities needed to make our short stay comfortable. The host was very responsive and accommodating. "
United States
Annette H.
The price is NZ$1,310
includes taxes & fees
20 Nov - 21 Nov
Peaceful Vintage Home with Private Lake in Redding, CT.

Stylish Sheek Loft Dwntwn, Amphitheater, Park, Metro North, Ferry All 2-10min

Downtown Bridgeport
10.0 out of 10, Exceptional, (1)
The price is NZ$289
includes taxes & fees
20 Nov - 21 Nov
Stylish Sheek Loft Dwntwn, Amphitheater, Park, Metro North, Ferry All 2-10min

DIRECT WATERFRONT with awesome views and near Yale

West Haven
10.0 out of 10, Exceptional, (2)
"Great place to stay! Easy for an overnight for a family wedding!"
United States
Phoebe T.
DIRECT WATERFRONT with awesome views and near Yale

Private Third-Floor Attic Apartment Full Kitchen • King Bed • Backyard Access

2.0 star property
West New Haven
9.0 out of 10, Wonderful, (2)
"Great communication and easy check in, would recommend "
United States
Ethan R.
The price is NZ$228
includes taxes & fees
20 Nov - 21 Nov
Private Third-Floor Attic Apartment Full Kitchen • King Bed • Backyard Access

Charming Home in Seaside

2.0 star property
South End
10.0 out of 10, Exceptional, (1)
"Amazing beautiful property in a rustic urban environment. Perfect check in, super comfortable, TVs in every room… essentially a new house. Close to the water and amphitheater. If you’re used to city life we’d recommend it, because we are!"
United States
Matt H.
Charming Home in Seaside

Charming Studio| Near Yale| Downtown New Haven

Downtown New Haven
9.0 out of 10, Wonderful, (10)
"A great place to stay during reunions! Prime campus-adjacent location, an easy walk to all things on campus!"
United States
Jason K.
The price is NZ$387
includes taxes & fees
20 Nov - 21 Nov
Charming Studio| Near Yale| Downtown New Haven

Beechmont - Perfect for Family Retreat!

5.0 star property
North End
The price is NZ$2,001
includes taxes & fees
20 Nov - 21 Nov
Beechmont - Perfect for Family Retreat!

Waterfront Cottage in Branford

branford
10.0 out of 10, Exceptional, (97)
"Such a beautiful home and amazing views! Stayed here with friends for a wedding and it was the most ideal. "
United States
Bradie S.
Waterfront Cottage in Branford

Adorable Beach Cottage

Milford
9.8 out of 10, Exceptional, (54)
"Lovely cottage, well equipped and immaculately clean, close to the beach and charming shops and restaurants. "
United States
Sarah G.
Adorable Beach Cottage

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

Milford
10.0 out of 10, Exceptional, (132)
"Wonderful stay in a nice quiet neighborhood "
United States
Jacob M.
Beach Front Arts & Crafts House With Gorgeous Views Of The Sound

New One Bedroom Apartment Centrally Located in Southbury

Southbury
9.8 out of 10, Exceptional, (17)
"Perfect sized apartment for a short stay - very convenient to my destination"
United States
S
The price is NZ$227
includes taxes & fees
23 Nov - 24 Nov
New One Bedroom Apartment Centrally Located in Southbury

Gorgeous 4BR Beach House with Private Beach Access.

Pine Orchard
9.8 out of 10, Exceptional, (75)
"Nice property, thanks to the owners.Jackie"
United States
Jacqueline M.
Gorgeous 4BR Beach House with Private Beach Access.

Stunning Apt W/ Parking and Gym | Downtown at Yale

The Hill
10.0 out of 10, Exceptional, (46)
"High quality experience, walking distance to all we needed, clean and spacious. Excellent support and communication from the hosts, would stay again."
United Kingdom
Coco N.
Stunning Apt W/ Parking and Gym | Downtown at Yale

Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.

Cheshire
9.2 out of 10, Wonderful, (11)
"Needed a place to sleep for a couple of nights and this worked for us."
United States
James (Jim) L.
The price is NZ$289
includes taxes & fees
20 Nov - 21 Nov
Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.

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

Brooklawn - St. Vincent
9.4 out of 10, Exceptional, (22)
"Beautifully appointed luxury 2 nd floor accommodations in the city of Bridgeport. Guests could comfortably stay for multiple nights with the well equipped kitchen and dining room space. "
United States
Tessa P.
The price is NZ$741
includes taxes & fees
24 Nov - 25 Nov
Luxury Designer 2 bedroom+office/3bed vacation home.
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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Find out more about Seymour

Everything you need to know about Seymour holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Seymour holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Seymour holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Seymour holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Seymour. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Seymour holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Seymour holiday rentals we have selected for you start as low as NZ$227 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Seymour rentals

At Expedia, we put the best Seymour holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Seymour rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Seymour holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Seymour. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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?

Lakeside/Sleeps20/HotTub/GameRoom/2Acres/Firepit: This holiday home rental outside of Seymour is located on a lake, and has a fireplace, a patio 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. It offers a garden, an arcade/games room and 1 hot tub so that you can immerse yourself in your 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 Beacon Falls Town Recreation Field and Ansonia Mall Shopping Center.

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.