Seymour Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
Dec 29 - Dec 30
Tomorrow
Dec 30 - Dec 31
This weekend
Jan 2 - Jan 4
Next weekend
Jan 9 - Jan 11

Our top choices for Seymour vacation rentals

Private beach nearby, sun loungers, beach umbrellas, beach towels
DUNE Fairfield Beach

DUNE Fairfield Beach

DUNE Fairfield Beach
3.0 star property
Fairfield Beach
9.0 out of 10, Wonderful, (78)
"The room was spotless and cozy and the location couldn't be better! "
United States
Samantha
DUNE Fairfield Beach
Private kitchen
Westville Stay • 2BR • Near Yale • Free Parking

Westville Stay • 2BR • Near Yale • Free Parking

Westville Stay • 2BR • Near Yale • Free Parking
West New Haven
10.0 out of 10, Exceptional, (3)
"We were only here for a short stay, but everything was smooth and comfortable for us! Hotel-like linens and blackout curtains made for a very cozy sleeping experience."
United States
ross f.
The price is ￥12,526
￥36,638 total
includes taxes & fees
Jan 8 - Jan 9, 2026
Westville Stay • 2BR • Near Yale • Free Parking
2 bedrooms, iron/ironing board, travel crib, WiFi
Renovated 2BR Retreat / Modern Comforts Included

Renovated 2BR Retreat / Modern Comforts Included

Renovated 2BR Retreat / Modern Comforts Included
West End - West Side
10.0 out of 10, Exceptional, (2)
"Very pretty, clean place for us to stay while visiting family. Communication was very timely. Would definitely stay here again"
United States
Deborah
The price is ￥16,571
￥45,518 total
includes taxes & fees
Dec 30 - Dec 31
Renovated 2BR Retreat / Modern Comforts Included
Exterior
New One Bedroom Apartment Centrally Located in Southbury

New One Bedroom Apartment Centrally Located in Southbury

New One Bedroom Apartment Centrally Located in Southbury
Southbury
9.8 out of 10, Exceptional, (20)
"Perfect sized apartment for a short stay - very convenient to my destination"
United States
S
The price is ￥13,387
￥18,527 total
includes taxes & fees
Dec 30 - Dec 31
New One Bedroom Apartment Centrally Located in Southbury
Exterior
Charming Studio| Near Yale| Downtown New Haven

Charming Studio| Near Yale| Downtown New Haven

Charming Studio| Near Yale| Downtown New Haven
Downtown New Haven
9.0 out of 10, Wonderful, (12)
"Convenient location. Just off Rte 91. Easy street parking. The studio is as pictured - exposed brick walls, high ceilings. Everything you need for a short stay. "
United States
Lois G.
The price is ￥11,899
￥29,591 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Charming Studio| Near Yale| Downtown New Haven
Cookware/dishes/utensils
Urban Oasis 3BR Parking Washer & Dryer Yale East Rock

Urban Oasis 3BR Parking Washer & Dryer Yale East Rock

Urban Oasis 3BR Parking Washer & Dryer Yale East Rock
East Rock
9.6 out of 10, Exceptional, (10)
"Thanks to the detailed information from the host check-in couldn’t have been easier. The home was clean and well-appointed. Great location with access to the Yale tram and local markets and restaurants. "
United States
Denyce D.
The price is ￥14,874
￥41,248 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Urban Oasis 3BR Parking Washer & Dryer Yale East Rock
Exterior
Green N' Groovy in the Heart of East Rock Near DT | Yale |Cozy N' Comfortable

Green N' Groovy in the Heart of East Rock Near DT | Yale |Cozy N' Comfortable

Green N' Groovy in the Heart of East Rock Near DT | Yale |Cozy N' Comfortable
East Rock
10.0 out of 10, Exceptional, (4)
"Great place - wish we had more than one night. "
United States
Steri-Clean N.
The price is ￥22,546
￥58,729 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Green N' Groovy in the Heart of East Rock Near DT | Yale |Cozy N' Comfortable
Interior
Private, Quiet, Cozy Studio Guesthouse with 75" TV WiFi etc. In Watertown.

Private, Quiet, Cozy Studio Guesthouse with 75" TV WiFi etc. In Watertown.

Private, Quiet, Cozy Studio Guesthouse with 75" TV WiFi etc. In Watertown.
Watertown
8.6 out of 10, Excellent, (10)
"Great night stay! Wonderful place would definitely recommend! "
United States
Laurie P.
The price is ￥13,935
￥19,157 total
includes taxes & fees
Jan 3 - Jan 4, 2026
Private, Quiet, Cozy Studio Guesthouse with 75" TV WiFi etc. In Watertown.
Fridge, microwave, oven, stovetop
Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.

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

Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.
Cheshire
9.4 out of 10, Exceptional, (13)
"Needed a place to sleep for a couple of nights and this worked for us."
United States
James (Jim) L.
The price is ￥13,387
￥25,729 total
includes taxes & fees
Dec 31 - Jan 1, 2026
Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.
Fridge, microwave, oven, stovetop
Welcoming 1500 square foot 3-bedroom house completely remodeled in Southington

Welcoming 1500 square foot 3-bedroom house completely remodeled in Southington

Welcoming 1500 square foot 3-bedroom house completely remodeled in Southington
Southington
10.0 out of 10, Exceptional, (1)
"We had a great, relaxing Thanksgiving holiday at this spacious Southington, CT home. It was the perfect spot to visit one of my daughters and be able to have my mother-in-law stay with us so we could cook and host Thanksgiving dinner. The house was well-stocked and supplied with everything we needed, and then some; which allowed us to have a stress-free holiday as if we were in our own home. We highly recommend this home and will keep it in mind for future extended stays in the area."
United States
Cindy M.
The price is ￥13,653
￥77,366 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Welcoming 1500 square foot 3-bedroom house completely remodeled in Southington
1 bedroom, desk, iron/ironing board, WiFi
One bedroom apartment in United States of America, New Haven

One bedroom apartment in United States of America, New Haven

One bedroom apartment in United States of America, New Haven
Dwight
9.4 out of 10, Exceptional, (3)
"Apartment was very clean and well supplied, host very responsive. Location is convenient to Yale and restaurants. As noted in the listing, you'll have to carry your luggage up 4 flights of stairs. There is some street noise as is typical for that part of the city. Very happy with it overall and plan to stay again."
United States
Philip S.
The price is ￥14,874
￥32,253 total
includes taxes & fees
Dec 30 - Dec 31
One bedroom apartment in United States of America, New Haven
Interior
The Nest At Elm City Flats.

The Nest At Elm City Flats.

The Nest At Elm City Flats.
West New Haven
9.4 out of 10, Exceptional, (6)
"Nice place! Short but sweet trip. Appreciate how quick your communication was and your accommodations!"
United States
Lori K.
The price is ￥13,950
￥36,593 total
includes taxes & fees
Dec 30 - Dec 31
The Nest At Elm City Flats.
Fridge, microwave, oven, stovetop
#16 *A COZY GETAWAY* 4BED/3BATH HOME W/ FIRE PIT

#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, (7)
"We enjoyed our stay! And happy with most!!!!"
United States
Dawn H.
The price is ￥46,741
￥90,703 total
includes taxes & fees
Jan 2 - Jan 3, 2026
#16 *A COZY GETAWAY* 4BED/3BATH HOME W/ FIRE PIT
1 bedroom, iron/ironing board, WiFi, bed sheets
Once the old Schools house now a newly furnished Apartment

Once the old Schools house now a newly furnished Apartment

Once the old Schools house now a newly furnished Apartment
Wallingford Center
9.0 out of 10, Wonderful, (13)
"Excellent option for a short stay near the heart of it all in Wallingford."
United States
Jeanette W.
The price is ￥18,006
￥45,132 total
includes taxes & fees
Jan 2 - Jan 3, 2026
Once the old Schools house now a newly furnished Apartment
Apartment (2 Bedrooms) | Interior
2 Mi to Beach, Shared Yard Space: West Haven Apt!

2 Mi to Beach, Shared Yard Space: West Haven Apt!

2 Mi to Beach, Shared Yard Space: West Haven Apt!
3.0 star property
West Haven
The price is ￥21,450
￥56,055 total
includes taxes & fees
Dec 30 - Dec 31
2 Mi to Beach, Shared Yard Space: West Haven Apt!
Fridge, microwave, oven, stovetop
Beach Apartment in Woodmont Milford

Beach Apartment in Woodmont Milford

Beach Apartment in Woodmont Milford
2.0 star property
Milford
9.0 out of 10, Wonderful, (2)
"Had a great stay!"
United States
Garry G.
The price is ￥20,041
￥60,076 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Beach Apartment in Woodmont Milford
1 bedroom, desk, iron/ironing board, free WiFi
Orange & Groovy Stylish Amphitheater, Park, Metro North, Ferry All 2-10min walk

Orange & Groovy Stylish Amphitheater, Park, Metro North, Ferry All 2-10min walk

Orange & Groovy Stylish Amphitheater, Park, Metro North, Ferry All 2-10min walk
Downtown Bridgeport
9.4 out of 10, Exceptional, (8)
"The apartment was very clean with everything we needed for our stay. Outside noise was a little loud so I’d suggest a sound machine, but in case your forget the awesome host has supplied soft ear plugs for you. I would definitely visit again. "
United States
Chrystie
The price is ￥21,920
￥36,011 total
includes taxes & fees
Jan 2 - Jan 3, 2026
Orange & Groovy Stylish Amphitheater, Park, Metro North, Ferry All 2-10min walk
Exterior
Spacious 2 Bedroom apartment close to Yale Bowl

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, (69)
"The apartment was very clean and convenient. Will definitely stay there again. "
United States
Joan S.
The price is ￥20,354
￥35,854 total
includes taxes & fees
Dec 30 - Dec 31
Spacious 2 Bedroom apartment close to Yale Bowl
Exterior
Angelica’s safe haven @ west haven

Angelica’s safe haven @ west haven

Angelica’s safe haven @ west haven
West Haven
10.0 out of 10, Exceptional, (6)
"Quiet place with spacious living room perfect for movie nights. Also just a 10-minute drive from the beach and multiple dining options. Host was very accommodating and communicative. Would stay here again."
United States
Veronica
The price is ￥19,305
￥48,153 total
includes taxes & fees
Dec 30 - Dec 31
Angelica’s safe haven @ west haven
Fridge, microwave, oven, stovetop
#26 Beautifully Renovated 2 BR Home

#26 Beautifully Renovated 2 BR Home

#26 Beautifully Renovated 2 BR Home
Plainville
10.0 out of 10, Exceptional, (4)
"We thoroughly enjoyed our stay! The space was great for our family of 4. Would recommend!"
United States
LaTanya W.
The price is ￥18,261
￥36,656 total
includes taxes & fees
Jan 5 - Jan 6, 2026
#26 Beautifully Renovated 2 BR 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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Seymour Hotel Reviews

Red Roof Inn Milford - New Haven

Red Roof Inn Milford - New Haven

10/10 Excellent
"Staff are very professional. "
Bermann 1-night trip
Posted 1 day ago
Red Roof Inn Milford - New Haven

Find out more about Seymour

Search for holiday rentals in Seymour on Expedia! You can easily find your home rentals, villas, holiday apartments in Seymour using one of the methods below:

  • View our selection of featured holiday rentals in Seymour
  • Use the map to find apartments and other holiday homes in the Seymour neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Seymour while they last

Look no further and take a look at our great range of rental properties in Seymour!

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?

Beach Front Arts & Crafts House With Gorgeous Views Of The Sound: This vacation home rental near Seymour is located on the beach and has a fireplace, a balcony, and a barbecue grill 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 you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

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.