Search Vacation Homes in Madison

  • 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

In two weeks
6 Feb - 8 Feb
In two months
20 Mar - 22 Mar
In three months
17 Apr - 19 Apr
In four months
15 May - 17 May

Our top choices for Madison vacation homes

Smart TV, books

Rogers Lake House (87) · CT College+Beach+USCGA

Rogers Lake House (87) · CT College+Beach+USCGA
Old Lyme
10.0 out of 10, Exceptional, (5 reviews)
"My family and I came for an 8 day event from a different state and wanted a clean and comfortable place to stay with our at the time 9 month old daughter. And this place did exactly that. Comfortable and CLEAN. The owner did a great job with details. Even when we had unexpected check out delays the owner showed human empathy. Great place!"
United States
Hemie J.
The price is AED 369
AED 1,538 total
includes taxes & fees
26 Jan - 27 Jan
Rogers Lake House (87) · CT College+Beach+USCGA
Beach nearby

The Bay Cottage · Rocky Neck Park, Beach & Niantic

The Bay Cottage · Rocky Neck Park, Beach & Niantic
East Lyme
9.0 out of 10, Wonderful, (4 reviews)
"This house suited our needs for a place to stay while attending a nearby family reunion. Communication and check in were great and the house is very comfortable (very nice mattresses, sheets, pillows)."
United States
Sarah G.
The price is AED 435
AED 1,338 total
includes taxes & fees
25 Feb - 26 Feb
The Bay Cottage · Rocky Neck Park, Beach & Niantic
Exterior

Family Stays: Middletown, CT

Family Stays: Middletown, CT
Middletown
10.0 out of 10, Exceptional, (20 reviews)
"A truly wonderful experience! The host and home were amazing and we’ll definitely be staying here again!"
United States
Harmony R.
The price is AED 441
AED 845 total
includes taxes & fees
2 Feb - 3 Feb
Family Stays: Middletown, CT
Property grounds

#24 *Serenity* A Lakefront Cottage Retreat

#24 *Serenity* A Lakefront Cottage Retreat
Middletown
9.8 out of 10, Exceptional, (21 reviews)
"We had a wonderful stay at this property! The house itself was beautiful—spacious, clean, and incredibly comfortable. The setting was just as impressive, offering peaceful views and a great atmosphere to relax and unwind. Everything was exactly as described, if not better. We would absolutely stay here again and highly recommend it to anyone looking for a serene and well-appointed home base for our stay. "
United States
Nichole N.
The price is AED 558
AED 1,244 total
includes taxes & fees
18 Feb - 19 Feb
#24 *Serenity* A Lakefront Cottage Retreat
Interior

Cozy Guest Suite in Historic Home

Cozy Guest Suite in Historic Home
Middletown
10.0 out of 10, Exceptional, (1 review)
"Perfect for a single traveler. Clean, roomy, quaint room. "
United States
Brooke
The price is AED 542
AED 789 total
includes taxes & fees
28 Jan - 29 Jan
Cozy Guest Suite in Historic Home
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
Southington
10.0 out of 10, Exceptional, (1 review)
"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 AED 320
AED 1,815 total
includes taxes & fees
26 Jan - 27 Jan
Welcoming 1500 square foot 3-bedroom house completely remodeled in Southington
Beach

Beachside Bliss w/ Game Room, Gym & Golf Green

Beachside Bliss w/ Game Room, Gym & Golf Green
Westbrook
10.0 out of 10, Exceptional, (1 review)
"Perfect house for 6 guests. Loved that it was close to the beach."
United States
Shannon G.
The price is AED 497
AED 1,847 total
includes taxes & fees
27 Jan - 28 Jan
Beachside Bliss w/ Game Room, Gym & Golf Green
Dining

LONG-TERM Skiing, Tubing 30 mins away and the Ocean 5 mins!

LONG-TERM Skiing, Tubing 30 mins away and the Ocean 5 mins!
Clinton
10.0 out of 10, Exceptional, (3 reviews)
"Beautiful home in a quiet neighborhood. We greatly enjoyed staying at Glass House. "
United States
Elya D.
The price is AED 492
AED 1,904 total
includes taxes & fees
10 Feb - 11 Feb
LONG-TERM Skiing, Tubing 30 mins away and the Ocean 5 mins!
Smart TV

Cozy East Haven Home • Near Beach & Yale

Cozy East Haven Home • Near Beach & Yale
Momauguin
10.0 out of 10, Exceptional, (5 reviews)
"Such a cute place, loved all the nautical touches. Great space for a weekend getaway, pretty well-stocked kitchen, clean & cozy. Really appreciated the outdoor space & amenities too! And Michael the host is very responsive & helpful! "
United States
Amal A.
The price is AED 413
AED 549 total
includes taxes & fees
3 Feb - 4 Feb
Cozy East Haven Home • Near Beach & Yale
Exterior

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 reviews)
"Excellent option for a short stay near the heart of it all in Wallingford."
United States
Jeanette W.
The price is AED 422
AED 1,059 total
includes taxes & fees
26 Jan - 27 Jan
Once the old Schools house now a newly furnished Apartment
2 bedrooms, WiFi, bed sheets

Private Apartment in Berlin

Private Apartment in Berlin
Berlin
9.2 out of 10, Wonderful, (5 reviews)
"Place was great, not to small and not to big. Beds were extremely comfortable. Berlin is a busy town but the house in tucked far enough away from it all. Great place and would gladly stay again! "
United States
Daniel L.
The price is AED 315
AED 1,015 total
includes taxes & fees
26 Jan - 27 Jan
Private Apartment in Berlin
Property grounds

Stylish Modern Stay Steps from the Ocean

Stylish Modern Stay Steps from the Ocean
Clinton
10.0 out of 10, Exceptional, (1 review)
"Very Clean and New. Location very convenient to Shopping , Coffee and Winery. Place very very small but Shower was huge and token gifts such as wine and toiletries a big plus . As well as guest for TV for Netflix. Added bonus outdoor space makes up for lack of living room. I would recommend this place and stay again for sure. Also, conveniently located to major highway and safe. "
United States
Kelly Z.
The price is AED 661
AED 1,326 total
includes taxes & fees
26 Jan - 27 Jan
Stylish Modern Stay Steps from the Ocean
3 bedrooms, desk, iron/ironing board, free WiFi

3BR Gem, 10 min to Yale, walk to Tweed

3BR Gem, 10 min to Yale, walk to Tweed
East Shore
10.0 out of 10, Exceptional, (3 reviews)
"The place was amazing! Honestly more than the picture shows. The house is a wooden and warm home. I could charge the temperature and unlock the door through the app. There was free wifi and the rooms were beautiful and comfortable. We had everything we needed and more for the kitchen. Amazing communication back and forward. A lot was already supplied in the home.I would say mt favorite thing was just the feeling of the place. They even had board game which we ended up enjoying so much. Would...
United States
jasmine L.
The price is AED 793
AED 1,978 total
includes taxes & fees
26 Jan - 27 Jan
3BR Gem, 10 min to Yale, walk to Tweed
Marina

Gorgeous Waterfront 3 Bedroom, 1.5 Bathroom Unit.

Gorgeous Waterfront 3 Bedroom, 1.5 Bathroom Unit.
Fair Haven
9.6 out of 10, Exceptional, (15 reviews)
"Had a really nice stay, enjoyed this open airy space with comfortable beds and beautiful light with a view of the river. Very nice time, would stay again."
United States
Brian B.
The price is AED 559
AED 1,087 total
includes taxes & fees
26 Jan - 27 Jan
Gorgeous Waterfront 3 Bedroom, 1.5 Bathroom Unit.
Smart TV

#29 - Modern 5 Bedroom/2 Bath

#29 - Modern 5 Bedroom/2 Bath
Middletown
9.4 out of 10, Exceptional, (6 reviews)
"Great place! "
United States
Gail R.
The price is AED 731
AED 1,674 total
includes taxes & fees
31 Jan - 1 Feb
#29 - Modern 5 Bedroom/2 Bath
Smart TV, fireplace, books, offices

Great Hammcock Getaway, cozy home, hot tub, fire pit, beaches nearby.

Great Hammcock Getaway, cozy home, hot tub, fire pit, beaches nearby.
Old Saybrook
9.8 out of 10, Exceptional, (8 reviews)
"This was the perfect house for our family’s long weekend getaway to coastal New England. The house was beautiful and spotless, and came with everything you might need and more. We loved the griddle, the hot tub and my son loved the game room. Would definitely stay again!"
United States
Doug F.
The price is AED 918
AED 1,840 total
includes taxes & fees
15 Feb - 16 Feb
Great Hammcock Getaway, cozy home, hot tub, fire pit, beaches nearby.
Terrace/patio

American Beech in Greenport - Petite King Room 7

American Beech in Greenport - Petite King Room 7
Greenport
9.0 out of 10, Wonderful, (4 reviews)
"We thoroughly enjoyed our stay!"
United States
Parent From The Heart, Inc. E.
The price is AED 437
AED 739 total
includes taxes & fees
27 Jan - 28 Jan
American Beech in Greenport - Petite King Room 7
Dining

Stocked home close to Yale, in Heart of New Haven

Stocked home close to Yale, in Heart of New Haven
Mill River
9.2 out of 10, Wonderful, (18 reviews)
"Great value very close to university. "
United States
Lawrence
The price is AED 545
AED 915 total
includes taxes & fees
26 Jan - 27 Jan
Stocked home close to Yale, in Heart of New Haven
Marina

Gorgeous Waterfront 2 Bedroom 1 Bath Modern Home.

Gorgeous Waterfront 2 Bedroom 1 Bath Modern Home.
Fair Haven
7.6 out of 10, Good, (5 reviews)
"Thanks for hosting us! It was clean and nice. For future guests, a long body mirror might be nice but we had a wonderful time and appreciated you bringing us extra towels quickly!"
United States
Jamie S.
The price is AED 423
AED 821 total
includes taxes & fees
26 Jan - 27 Jan
Gorgeous Waterfront 2 Bedroom 1 Bath Modern Home.
Terrace/patio

The Jewel of The Cove - Historic Coastal Retreat

The Jewel of The Cove - Historic Coastal Retreat
East Shore
9.8 out of 10, Exceptional, (7 reviews)
"loved it so much, beautiful property 100 % would stay again "
United States
Leilani R.
The price is AED 760
AED 1,895 total
includes taxes & fees
3 Feb - 4 Feb
The Jewel of The Cove - Historic Coastal Retreat
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 Madison Hotel Reviews

Hotel Marcel New Haven, Tapestry Collection By Hilton

Hotel Marcel New Haven, Tapestry Collection By Hilton

10/10 Excellent
"The hotel was very clean self parking easy and conveniently located. "
Amber 1-night trip
Posted 2 days ago
Hotel Marcel New Haven, Tapestry Collection By Hilton