A waterfall cascading over rocks into a river, surrounded by lush green trees.

Seymour Vacation Rentals

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Our top choices for Seymour vacation rentals

Watertown Home w/ Yard: 1 Mi to Echo Lake Park!

Watertown Home w/ Yard: 1 Mi to Echo Lake Park!
3.0 star property
Oakville
$469 nightly
The price is $539
Jul 31 - Aug 1
Total with taxes and fees
Watertown Home w/ Yard: 1 Mi to Echo Lake Park!

Clear LI Sound waterview, Wedding pics, Yale&Beach

Clear LI Sound waterview, Wedding pics, Yale&Beach
East Shore
10.0 out of 10, Exceptional, (11 reviews)
"Great stay! Would definitely stay again! "
United States
Frankie O.
$857 nightly
The price is $972
Jul 20 - Jul 21
Total with taxes and fees
Clear LI Sound waterview, Wedding pics, Yale&Beach

Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!
5.0 star property
North End
$889 nightly
The price is $1,023
Jul 26 - Jul 27
Total with taxes and fees
Beechmont - Perfect for Family Retreat!

Elite room stay

Elite room stay
Bridgeport
$305 nightly
The price is $345
Jul 20 - Jul 21
Total with taxes and fees
Elite room stay

#43- Modern Luxury Log Cabin Retreat | Fire Pit

#43- Modern Luxury Log Cabin Retreat | Fire Pit
Prospect
9.0 out of 10, Wonderful, (2 reviews)
"3.5 rounding up to 4. We had a good stay overall. I travel fairly often and tend to reserve 5 stars for places where every detail of the guest experience feels really thoughtfully considered. This home was comfortable and worked fine for our trip, but it felt a bit more basic compared to some other rentals I’ve stayed in."
United States
Lauren P.
$661 nightly
The price is $724
Jul 24 - Jul 25
Total with taxes and fees
#43- Modern Luxury Log Cabin Retreat | Fire Pit

Coastal Landing Stay

Coastal Landing Stay
East Shore
$523 nightly
The price is $567
Jul 21 - Jul 22
Total with taxes and fees
Coastal Landing Stay

Centric property close to all the great things in the city

Centric property close to all the great things in the city
Brooklawn - St. Vincent
7.2 out of 10, Good, (15 reviews)
"Having a microwave would also help with the amenities. Overall good. "
United States
Karen A.
$237 nightly
The price is $268
Jul 22 - Jul 23
Total with taxes and fees
Centric property close to all the great things in the city

Angelica’s safe haven @ west haven

Angelica’s safe haven @ west haven
West Haven
10.0 out of 10, Exceptional, (6 reviews)
"We had a great stay. Comfortable home with a large living room. Beds were great. "
United States
Jason V.
$307 nightly
The price is $348
Jul 22 - Jul 23
Total with taxes and fees
Angelica’s safe haven @ west haven

DUNE Fairfield Beach

DUNE Fairfield Beach
3.0 star property
Fairfield Beach
9.0 out of 10, Wonderful, (99 reviews)
"Staff is excellent very clean and comfortable. Nice pla e with great beach access!"
United States
Stacie
$244 nightly
The price is $280
Aug 19 - Aug 20
Total with taxes and fees
DUNE Fairfield Beach

Heavenly Home in New Haven /5 mins drive from Yale

Heavenly Home in New Haven /5 mins drive from Yale
Fair Haven
9.2 out of 10, Wonderful, (23 reviews)
"This house has everything you need to enjoy a getaway. Clean, It will sleep 20 and their is room for 20 to gather."
United States
Kathy B.
$712 nightly
The price is $802
Jul 26 - Jul 27
Total with taxes and fees
Heavenly Home in New Haven /5 mins drive from Yale

4 Mi to Beach & Dtwn! Charming Fairfield Home

4 Mi to Beach & Dtwn! Charming Fairfield Home
3.0 star property
Tunxis Hill
$567 nightly
The price is $652
Aug 2 - Aug 3
Total with taxes and fees
4 Mi to Beach & Dtwn! Charming Fairfield Home

Oceanfront Couples Retreat - Pvt Beach + Firepit

Oceanfront Couples Retreat - Pvt Beach + Firepit
Morgan Point
10.0 out of 10, Exceptional, (15 reviews)
"Gorgeous location on LI sound! The home was perfect for us. We had plenty of room to spread out and we relax. We enjoyed the deck and the bar area! We all slept very well and we actually loved watching the planes overhead! Lots of fun spots nearby to explore and are already hoping to come back in the fall. "
United States
Carrie R.
$1,134 nightly
The price is $1,282
Aug 1 - Aug 2
Total with taxes and fees
Oceanfront Couples Retreat - Pvt Beach + Firepit

#16 *A COZY GETAWAY* 4BED/3BATH HOME W/ FIRE PIT

#16 *A COZY GETAWAY* 4BED/3BATH HOME W/ FIRE PIT
Southington
9.0 out of 10, Wonderful, (8 reviews)
"We enjoyed our stay! And happy with most!!!!"
United States
Dawn H.
$474 nightly
The price is $511
Jul 28 - Jul 29
Total with taxes and fees
#16 *A COZY GETAWAY* 4BED/3BATH HOME W/ FIRE PIT

Modern home with a private Heated pool and jacuzzi

Modern home with a private Heated pool and jacuzzi
Hamden
$1,173 nightly
The price is $1,173
Aug 2 - Aug 3
Total with taxes and fees
Modern home with a private Heated pool and jacuzzi

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

Lovely Bohemian Loft Downtwn, Amphitheater,Seaside Park,Metro North,2-10min walk
Downtown Bridgeport
9.8 out of 10, Exceptional, (13 reviews)
"I was surprised by the large size of this apt, and that it had everything I needed for my stay. The location was perfect and very close to the event I was there for. Excellent host and I'm looking forward to booking this place again next year."
United States
Shamel
$174 nightly
The price is $197
Jul 20 - Jul 21
Total with taxes and fees
Lovely Bohemian Loft Downtwn, Amphitheater,Seaside Park,Metro North,2-10min walk

Gorgeous Waterfront 2:1 - 2 houses in 1 building.

Gorgeous Waterfront 2:1 - 2 houses in 1 building.
Fair Haven
$756 nightly
The price is $833
Jul 20 - Jul 21
Total with taxes and fees
Gorgeous Waterfront 2:1 - 2 houses in 1 building.

Cozy 1-bedroom house in welcoming Bridgeport

Cozy 1-bedroom house in welcoming Bridgeport
Bridgeport
$426 nightly
The price is $482
Jul 20 - Jul 21
Total with taxes and fees
Cozy 1-bedroom house in welcoming Bridgeport

3-bedroom house just walking distance from Yale and Downtown

3-bedroom house just walking distance from Yale and Downtown
Dixwell
10.0 out of 10, Exceptional, (4 reviews)
"Great stay!"
United States
Mark S.
$399 nightly
The price is $452
Jul 20 - Jul 21
Total with taxes and fees
3-bedroom house just walking distance from Yale and Downtown

Beach Apartment in Woodmont Milford 102

Beach Apartment in Woodmont Milford 102
Milford
$263 nightly
The price is $298
Jul 20 - Jul 21
Total with taxes and fees
Beach Apartment in Woodmont Milford 102

#41- Available 12/8! - sleeps 14

#41- Available 12/8! - sleeps 14
Southington
$529 nightly
The price is $569
Jul 22 - Jul 23
Total with taxes and fees
#41- Available 12/8! - sleeps 14
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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Top Seymour Hotel Reviews

Find out more about Seymour

Everything you need to know about Seymour vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Seymour vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Seymour vacation 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 low season months. For more hustle and bustle, you may prefer to visit Seymour in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Seymour rentals

At Expedia, we put the best Seymour vacation 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 vacation.

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.

Explore a world of travel with Expedia

Frequently asked questions

Are there vacation rentals in Seymour?

Yes, there are vacation rentals in Seymour near Waterski Connecticut, or you can choose a more remote 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 vacation home rentals in Seymour?

Charming Home in Seaside: This vacation home rental near Seymour is equipped with a patio, air-conditioning, and laundry facilities to help you feel comfortable during your stay. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

How many vacation rentals will I find in Seymour?

Choose from 4 Expedia vacation rentals in Seymour for a memorable vacation.

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 larger area, you’ll find Indian Well State Park and Southern Connecticut State University.

What are vacation rentals like in Seymour?

Vacation rentals are privately owned accommodations you can stay in for several days or longer in Seymour. Vacation rentals provide amenities like WiFi and washers and dryers so you'll have all the comforts of home. If you're concerned about a sanitized environment, vacation rentals can provide a sense of seclusion away from public hotel elevators and busy reception areas while still allowing you the experience of travel. You'll also find more space in a vacation rental than in a hotel, which is another reason why a vacation rental is an attractive option for small groups.