Seymour Vacation Rentals

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Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

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
The price is CA $180
CA $289 total
includes taxes & fees
Dec 2 - Dec 3
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
9.2 out of 10, Wonderful, (7 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.
The price is CA $165
CA $352 total
includes taxes & fees
Dec 1 - Dec 2
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.
The price is CA $191
CA $383 total
includes taxes & fees
Dec 1 - Dec 2
Private Apartment in Southbury 101
A neatly arranged bedroom with a bed, a bedside lamp, a nightstand, a dresser, and a window with curtains.

4. Modern Westville Home near Yale and Hospitals

Modern Westville Home near Yale and Hospitals
West New Haven
10.0 out of 10, Exceptional, (5 reviews)
"Very clean and comfortable space. Excellent location and parking was a plus. We have stayed here twice and would definitely recommend to friends or family. "
United States
Thomas B.
The price is CA $132
CA $321 total
includes taxes & fees
Nov 9 - Nov 10
Modern Westville Home near Yale and Hospitals
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.

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

Luxurious-Modern feel w/ custom features - AC, short walk to Shelton
Shelton
The price is CA $210
CA $617 total
includes taxes & fees
Nov 9 - Nov 10
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.

6. 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, (80 reviews)
"Clean, thoughtful, safe. Great stay"
United States
Daniel S.
The price is CA $162
CA $285 total
includes taxes & fees
Nov 9 - Nov 10
Spacious 2 Bedroom apartment close to Yale Bowl
A modern kitchen with a central island, stainless steel appliances, and pendant lighting.

7. Stylish Westville Apartment near Yale Campus

Stylish Westville Apartment near Yale Campus
West New Haven
9.2 out of 10, Wonderful, (5 reviews)
"Convenient location & hosts"
United States
Northeast C.
The price is CA $132
CA $325 total
includes taxes & fees
Nov 9 - Nov 10
Stylish Westville Apartment near Yale Campus
Interior

8. 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.
The price is CA $111
CA $252 total
includes taxes & fees
Nov 9 - Nov 10
Château Blanc | Near Yale University
A white house with a wooden staircase leading to a porch.

9. Cozy One Bedroom Apartment Centrally Located in Southbury

Cozy One Bedroom Apartment Centrally Located in Southbury
Southbury
10.0 out of 10, Exceptional, (39 reviews)
"Charles was super responsive and the bed was amazingly comfortable. Also the shower head great water pressure :-)"
United States
Lisbeth
The price is CA $134
CA $171 total
includes taxes & fees
Nov 20 - Nov 21
Cozy One Bedroom Apartment Centrally Located in Southbury
A bedroom with a bed, a blue sofa, a radiator, a window with blinds, a dreamcatcher, and a framed picture on the wall.

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

One bedroom in United States of America, New Haven
Dwight
9.4 out of 10, Exceptional, (3 reviews)
"The property is immaculate and the service very responsive."
United States
Stephanie G.
The price is CA $112
CA $246 total
includes taxes & fees
Dec 7 - Dec 8
One bedroom in United States of America, New Haven
A hallway with three elevators, each with a doorbell and a small sign above the door.

11. Yale Deluxe Modern Apartment

Yale Deluxe Modern Apartment
Downtown New Haven
10.0 out of 10, Exceptional, (1 review)
"Great spot close to everything with a secure entrance to the building. Easy access to the unit Quick responses and good communication from the host. Great unit with lots of amenities! Definitely would stay here again and again!!"
United States
Anonymous traveller
The price is CA $111
CA $241 total
includes taxes & fees
Nov 9 - Nov 10
Yale Deluxe Modern Apartment
A neatly made bed with a checkered blanket, white pillows, and a framed picture on the wall.

12. 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
The price is CA $108
CA $241 total
includes taxes & fees
Nov 30 - Dec 1
Yale Casa Verde Studio
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.

13. 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.
The price is CA $139
CA $316 total
includes taxes & fees
Nov 15 - Nov 16
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.

14. 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.
The price is CA $191
CA $384 total
includes taxes & fees
Nov 9 - Nov 10
Spacious Bohemian Nook
A house with a front porch, a garage, and a well-maintained lawn.

15. 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.
The price is CA $212
CA $481 total
includes taxes & fees
Nov 20 - Nov 21
Angelica’s safe haven @ west haven
A row of brownstone buildings with a central staircase leading to the second floor.

16. Bright Downtown Studio near Yale & East Rock!

Bright Downtown Studio near Yale & East Rock!
Downtown New Haven
9.2 out of 10, Wonderful, (17 reviews)
"Pretty close to Yale campus"
United States
Dongjian
The price is CA $146
CA $321 total
includes taxes & fees
Nov 9 - Nov 10
Bright Downtown Studio near Yale & East Rock!
A rooftop patio with outdoor seating, string lights, and a city skyline view.

17. 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)
"Very clean and accessible and amenities were excellent."
United States
Andrea H.
The price is CA $178
CA $290 total
includes taxes & fees
Nov 9 - Nov 10
Modern Elegant Stay by Yale • Gym • Rooftop Terrace
A row of brick townhouses with wooden front doors, black railings, and a sidewalk.

18. Prime Yale Studio Steps to Sallys Apizza

Prime Yale Studio Steps to Sallys Apizza
Downtown New Haven
10.0 out of 10, Exceptional, (2 reviews)
"Great stay - and it is close to Sally's! We had a nice visit and all was as represented for the property."
United States
Milton W.
The price is CA $158
CA $347 total
includes taxes & fees
Nov 17 - Nov 18
Prime Yale Studio Steps to Sallys Apizza
A living room with a wooden floor, a television on a white stand, a dining table with books, and a chair with a blanket.

19. Yale Science Park 1BR | Free Parking

Yale Science Park 1BR | Free Parking
Dixwell
8.0 out of 10, Very good, (8 reviews)
"The property had everything needed and was a short distance to so many campus sites. Would definitely stay again."
United States
Natalie B.
The price is CA $182
CA $370 total
includes taxes & fees
Nov 15 - Nov 16
Yale Science Park 1BR | Free Parking
A two-story house with a porch, a front door with a wreath, and a small garden area.

20. Bear Retreat - 2-bedroom house in Waterbury

Bear Retreat - 2-bedroom house in Waterbury
Waterbury
10.0 out of 10, Exceptional, (13 reviews)
"Perfect, spacious area. Super clean. Communication was great. Would definitely book here again."
United States
Radha
The price is CA $164
CA $465 total
includes taxes & fees
Nov 22 - Nov 23
Bear Retreat - 2-bedroom house in Waterbury
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 vacation rentals that suit your style

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Cabins
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Top Seymour Hotel Reviews

An outdoor patio area with a stone fire pit, wicker furniture, and a bar area with a flat-screen TV.
Residence Inn by Marriott New Haven Hamden

Residence Inn by Marriott New Haven Hamden

Residence Inn by Marriott New Haven Hamden
Hamden

10/10 Excellent

Clean room
Canada
Jintong
Reviewed October 30, 2026
Residence Inn by Marriott New Haven Hamden

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, 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 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 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 vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Seymour vacation rentals we have selected for you start as low as CA $107 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 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.

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.