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 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

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
$192 nightly
The price is $218
Oct 19 - Oct 20
Total with taxes and fees
Serene Country Cottage
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.

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

Luxurious-Modern feel w/ custom features - AC, short walk to Shelton
Shelton
$393 nightly
The price is $447
Nov 2 - Nov 3
Total with taxes and fees
Luxurious-Modern feel w/ custom features - AC, short walk to Shelton
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.
$248 nightly
The price is $281
Nov 17 - Nov 18
Total with taxes and fees
Private Apartment in Southbury 101
A modern kitchen with white cabinets, a black countertop, and a dining area with a table and chairs.

4. 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.
$234 nightly
The price is $265
Nov 17 - Nov 18
Total with taxes and fees
Private Apartment in Southbury 102
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, (80 reviews)
"Clean, thoughtful, safe. Great stay"
United States
Daniel S.
$185 nightly
The price is $209
Oct 26 - Oct 27
Total with taxes and fees
Spacious 2 Bedroom apartment close to Yale Bowl
A modern apartment with a green sofa, a wooden dining table, and a kitchen in the background.

6. 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.
$215 nightly
The price is $244
Nov 2 - Nov 3
Total with taxes and fees
Modern Westville Home near Yale and Hospitals
A white house with a wooden staircase leading to a porch.

7. 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.
$124 nightly
The price is $139
Oct 18 - Oct 19
Total with taxes and fees
Cozy One Bedroom Apartment Centrally Located in Southbury
A white living room with a sofa, a coffee table, and a bookshelf.

8. Expansive New Haven Home | Near Yale University

Expansive New Haven Home | Near Yale University
West New Haven
9.4 out of 10, Exceptional, (3 reviews)
"This property was perfect for our large group. It was clean, spacious and close to Yale. The backyard was another great space to relax. The owner was incredible! Answered all questions very quickly and very accommodating! We would recommend this property."
United States
Steve V.
$522 nightly
The price is $591
Oct 21 - Oct 22
Total with taxes and fees
Expansive New Haven Home | Near Yale University
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.

9. 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.
$225 nightly
The price is $254
Oct 18 - Oct 19
Total with taxes and fees
Spacious Bohemian Nook
A two-story house with a porch, a front door with a wreath, and a small garden area.

10. Bear Retreat - 2-bedroom house in Waterbury

Bear Retreat - 2-bedroom house in Waterbury
Waterbury
10.0 out of 10, Exceptional, (11 reviews)
"Perfect, spacious area. Super clean. Communication was great. Would definitely book here again."
United States
Radha
$300 nightly
The price is $340
Oct 18 - Oct 19
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.

11. 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.
$313 nightly
The price is $354
Oct 21 - Oct 22
Total with taxes and fees
Angelica’s safe haven @ west haven
A bedroom with a bed, a blue sofa, a radiator, a window with blinds, a dreamcatcher, and a framed picture on the wall.

12. 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.
$153 nightly
The price is $173
Oct 26 - Oct 27
Total with taxes and fees
One bedroom in United States of America, New Haven
A kitchen with white cabinets, a stove, and a dining table with chairs.

13. 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.
$215 nightly
The price is $244
Oct 18 - Oct 19
Total with taxes and fees
Yale Science Park 1BR | Free Parking
A living room with a gray sofa, black and white patterned pillows, a glass coffee table, a black and white rug, a fireplace, and a wall clock.

14. Spacious 3-bedroom apartment near Yale

Spacious 3-bedroom apartment near Yale
Dwight
10.0 out of 10, Exceptional, (1 review)
"Just an amazing place. Well thought out! Had everything we needed and even things we didn’t know we needed."
United States
Lara L.
$341 nightly
The price is $386
Oct 26 - Oct 27
Total with taxes and fees
Spacious 3-bedroom apartment near Yale
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.

15. 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.
$214 nightly
The price is $242
Oct 18 - Oct 19
Total with taxes and fees
The Sicilian
A row of brick townhouses with wooden front doors, black railings, and a sidewalk.

16. 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.
$191 nightly
The price is $216
Oct 19 - Oct 20
Total with taxes and fees
Prime Yale Studio Steps to Sallys Apizza
A modern building with large glass windows, a curved entrance, and a well-lit outdoor area with trees.

17. Casa Soleada in Heart of East Rock 3BR | Cozy King Bed | Near DT/Yale

Casa Soleada in Heart of East Rock 3BR | Cozy King Bed | Near DT/Yale
East Rock
10.0 out of 10, Exceptional, (11 reviews)
"Our 2 night stay was great. We were there for daughter's graduation from University of New Haven. Neighborhood was so quaint with lots of places to walk to. Place was very clean and accommodating. We would stay again!"
United States
Kathryn C.
$420 nightly
The price is $475
Oct 26 - Oct 27
Total with taxes and fees
Casa Soleada in Heart of East Rock 3BR | Cozy King Bed | Near DT/Yale
A neatly made bed with a checkered blanket, white pillows, and a framed picture on the wall.

18. 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
$160 nightly
The price is $181
Nov 2 - Nov 3
Total with taxes and fees
Yale Casa Verde Studio
A modern building with reflective glass facades, a central atrium, and a landscaped area with trees and pathways.

19. GreenN'Groovy: East Rock 5 mins to DT|Yale 5 beds

GreenN'Groovy: East Rock 5 mins to DT|Yale 5 beds
East Rock
10.0 out of 10, Exceptional, (4 reviews)
"Perfect for families."
United States
Frances
$379 nightly
The price is $428
Oct 28 - Oct 29
Total with taxes and fees
GreenN'Groovy: East Rock 5 mins to DT|Yale 5 beds
A rooftop terrace with tables, chairs, string lights, and a flat-screen TV.

20. Luxury 2BR New Haven Apt Near Yale w/ Rooftop, Gym & Parking

Luxury 2BR New Haven Apt Near Yale w/ Rooftop, Gym & Parking
Dwight
10.0 out of 10, Exceptional, (4 reviews)
"Great stay"
United States
Marquita M.
$219 nightly
The price is $247
Oct 18 - Oct 19
Total with taxes and fees
Luxury 2BR New Haven Apt Near Yale w/ Rooftop, Gym & Parking
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

Cambria Hotel New Haven University Area

Cambria Hotel New Haven University Area

10/10 Excellent
"It was great no issues. Hyygggg"
Michael 1-night trip
Posted 10 hours ago
Cambria Hotel New Haven University Area

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 $79 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.