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

Seymour Vacation Rentals

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Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Seymour vacation rentals

A kitchen with white cabinets, a black refrigerator, a double sink, and a window overlooking a wooded area.

1. Serene Country Cottage

Serene Country Cottage
Woodbridge
8.0 out of 10, Very good, (11 reviews)
"We had a great one night stay here! The place is really cute, clean and comfortable. One of the greatest parts about the stay was the host, Trent. He was welcoming and VERY responsive to questions! "
United States
felicia
$191 nightly
The price is $217
Oct 5 - Oct 6
Total with taxes and fees
Serene Country Cottage
A modern kitchen with white cabinets, a black countertop, and a dining area with a table and chairs.

2. Private Apartment in Southbury 102

Private Apartment in Southbury 102
Southbury
9.0 out of 10, Wonderful, (6 reviews)
"Over all a great place. Nice to have everything on one floor. Dogs loved it. Some businesses in the building and everyone is friendly!"
United States
Debbie P.
$243 nightly
The price is $275
Nov 3 - Nov 4
Total with taxes and fees
Private Apartment in Southbury 102
A view through a window with a clear sky and lush greenery outside.

3. Private Apartment in Southbury 101

Private Apartment in Southbury 101
Southbury
9.6 out of 10, Exceptional, (7 reviews)
"The apartment was nice, big area, loved this rental."
United States
Marissa G.
$257 nightly
The price is $291
Oct 28 - Oct 29
Total with taxes and fees
Private Apartment in Southbury 101
A modern living room with hardwood flooring, a leather sofa, a round coffee table, and a wooden side table. There is a dining area with a table and chairs visible in the background.

4. Luxurious-Modern feel w/ custom features - AC, short walk to Shelton

Luxurious-Modern feel w/ custom features - AC, short walk to Shelton
Shelton
$373 nightly
The price is $425
Oct 5 - Oct 6
Total with taxes and fees
Luxurious-Modern feel w/ custom features - AC, short walk to Shelton
A dining area with a long table, four chairs, a chandelier, and a painting on the wall.

5. Spacious 2 Bedroom apartment close to Yale Bowl

Spacious 2 Bedroom apartment close to Yale Bowl
West New Haven
9.6 out of 10, Exceptional, (79 reviews)
"Clean, thoughtful, safe. Great stay"
United States
Daniel S.
$183 nightly
The price is $207
Oct 5 - Oct 6
Total with taxes and fees
Spacious 2 Bedroom apartment close to Yale Bowl
A white house with a wooden staircase leading to a porch.

6. Cozy One Bedroom Apartment Centrally Located in Southbury

Cozy One Bedroom Apartment Centrally Located in Southbury
Southbury
10.0 out of 10, Exceptional, (37 reviews)
"Great place. Had everything we needed and was very clean."
United States
Niki B.
$106 nightly
The price is $118
Oct 14 - Oct 15
Total with taxes and fees
Cozy One Bedroom Apartment Centrally Located in Southbury
A living room with a flat-screen TV mounted on the wall, a yellow armchair, a patterned rug, and various decorative items on shelves and side tables.

7. The Sicilian

The Sicilian
West New Haven
9.2 out of 10, Wonderful, (17 reviews)
"It was the perfect day and very convenient for our trip for our son’s graduation. Thank you for being so receptive and helpful."
United States
Michele B.
$212 nightly
The price is $240
Oct 5 - Oct 6
Total with taxes and fees
The Sicilian
A cozy living room with a grey sofa, a coffee table with books and a vase of flowers, and bookshelves filled with books and decorative items.

8. Spacious Bohemian Nook

Spacious Bohemian Nook
West New Haven
8.4 out of 10, Very good, (9 reviews)
"We had a good time. Did some relaxing, a little beachtime and ate some good food."
United States
Erin S.
$224 nightly
The price is $253
Oct 5 - Oct 6
Total with taxes and fees
Spacious Bohemian Nook
A bedroom with a bed, a blue sofa, a radiator, a window with blinds, a dreamcatcher, and a framed picture on the wall.

9. One bedroom in United States of America, New Haven

One bedroom in United States of America, New Haven
Dwight
9.0 out of 10, Wonderful, (2 reviews)
"We enjoyed our stay. The accommodations were clean and spacious and communication was quick and helpful. Would definitely come back!"
United States
Rosanne M.
$154 nightly
The price is $174
Nov 2 - Nov 3
Total with taxes and fees
One bedroom in United States of America, New Haven
A neatly made bed with a checkered blanket, white pillows, and a framed picture on the wall.

10. Yale Casa Verde Studio

Yale Casa Verde Studio
Dwight
9.2 out of 10, Wonderful, (15 reviews)
"We had a very nice stay here! The hosts were lovely and very communicative, and they were able to help us with any problems we had very quickly."
United States
Luke
$164 nightly
The price is $186
Nov 2 - Nov 3
Total with taxes and fees
Yale Casa Verde Studio
A two-story house with a porch, a front door with a wreath, and a small garden area.

11. Bear Retreat - 2-bedroom house in Waterbury

Bear Retreat - 2-bedroom house in Waterbury
Waterbury
10.0 out of 10, Exceptional, (9 reviews)
"Perfect, spacious area. Super clean. Communication was great. Would definitely book here again."
United States
Radha
$300 nightly
The price is $340
Oct 5 - Oct 6
Total with taxes and fees
Bear Retreat - 2-bedroom house in Waterbury
A house with a front porch, a garage, and a well-maintained lawn.

12. Angelica’s safe haven @ west haven

Angelica’s safe haven @ west haven
West Haven
10.0 out of 10, Exceptional, (9 reviews)
"We had a great stay. Comfortable home with a large living room. Beds were great. "
United States
Jason V.
$311 nightly
The price is $352
Oct 6 - Oct 7
Total with taxes and fees
Angelica’s safe haven @ west haven
Interior

13. Château Blanc | Near Yale University

Château Blanc | Near Yale University
Dwight
8.6 out of 10, Excellent, (9 reviews)
"Perfect for a quick trip and one night stay!"
United States
Chris D.
$169 nightly
The price is $191
Nov 1 - Nov 2
Total with taxes and fees
Château Blanc | Near Yale University
A rooftop patio with outdoor seating, string lights, and a city skyline view.

14. Modern Elegant Stay by Yale • Gym • Rooftop Terrace

Modern Elegant Stay by Yale • Gym • Rooftop Terrace
Dwight
10.0 out of 10, Exceptional, (9 reviews)
"This was our second stay. Clean, excellent location and owner is the best! Will book again!"
United States
Kelly E.
Modern Elegant Stay by Yale • Gym • Rooftop Terrace
A compact kitchen with white cabinets, a stainless steel stove, a microwave, and a dishwasher.

15. Spa Inspired - 3BR Comfort Suite - Near Yale

Spa Inspired - 3BR Comfort Suite - Near Yale
Prospect Hill
8.6 out of 10, Excellent, (9 reviews)
"Beautiful place to stay in"
United States
Leo D.
$321 nightly
The price is $364
Oct 7 - Oct 8
Total with taxes and fees
Spa Inspired - 3BR Comfort Suite - Near Yale
A spacious lobby with a large chandelier, a central round table with a vase, and a checkered floor.

16. Yale Deluxe Modern Apartment

Yale Deluxe Modern Apartment
Downtown New Haven
$177 nightly
The price is $177
Oct 26 - Oct 27
Total with taxes and fees
Yale Deluxe Modern Apartment
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

Hilton Garden Inn Shelton

Hilton Garden Inn Shelton

10/10 Excellent
"Convenient."
Kemly 2-night trip
Posted 1 hour ago
Hilton Garden Inn Shelton

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 $152 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?

Beautiful, Spacious, Beachfront Home - Perfect for Entertaining Family & Friends: This vacation home rental near Seymour is located on the beach and has a balcony, a selection of games, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

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 Beacon Falls Town Recreation Field and Osborndale State Park.

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.