Holiday Homes in Madison

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Check prices for these dates

In two weeks
13 Feb - 15 Feb
In two months
27 Mar - 29 Mar
In three months
24 Apr - 26 Apr
In four months
22 May - 24 May

Our top choices for Madison holiday homes

Property grounds

Holiday Home in Middletown

#24 *Serenity* A Lakefront Cottage Retreat
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 €258
includes taxes & fees
30 Jan - 31 Jan
#24 *Serenity* A Lakefront Cottage Retreat
Smart TV, books

Holiday Home in Old Lyme

Rogers Lake House (87) · CT College+Beach+USCGA
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 €344
includes taxes & fees
1 Feb - 2 Feb
Rogers Lake House (87) · CT College+Beach+USCGA
TV

Holiday Home in Wallingford Center

Once the old Schools house now a newly furnished Apartment
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 €245
includes taxes & fees
30 Jan - 31 Jan
Once the old Schools house now a newly furnished Apartment
Beach nearby

Holiday Home in East Lyme

The Bay Cottage · Rocky Neck Park, Beach & Niantic
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 €305
includes taxes & fees
1 Mar - 2 Mar
The Bay Cottage · Rocky Neck Park, Beach & Niantic
Property grounds

Holiday Home in Clinton

Stylish Modern Stay Steps from the Ocean
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 €300
includes taxes & fees
30 Jan - 31 Jan
Stylish Modern Stay Steps from the Ocean
Beach

Holiday Home in Westbrook

Beachside Bliss w/ Game Room, Gym & Golf Green
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 €411
includes taxes & fees
4 Feb - 5 Feb
Beachside Bliss w/ Game Room, Gym & Golf Green
Interior

Holiday Home in Middletown

Cozy Guest Suite in Historic Home
10.0 out of 10, Exceptional, (1 review)
"Perfect for a single traveler. Clean, roomy, quaint room. "
United States
Brooke
The price is €183
includes taxes & fees
31 Jan - 1 Feb
Cozy Guest Suite in Historic Home
Exterior

Holiday Home in Middletown

Family Stays: Middletown, CT
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 €193
includes taxes & fees
9 Feb - 10 Feb
Family Stays: Middletown, CT
Smart TV

Holiday Home in Momauguin

Cozy East Haven Home • Near Beach & Yale
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 €128
includes taxes & fees
3 Feb - 4 Feb
Cozy East Haven Home • Near Beach & Yale
Dining

Holiday Home in Clinton

LONG-TERM Skiing, Tubing 30 mins away and the Ocean 5 mins!
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 €419
includes taxes & fees
10 Feb - 11 Feb
LONG-TERM Skiing, Tubing 30 mins away and the Ocean 5 mins!
Fridge, microwave, oven, stovetop

Holiday Home in Southington

Welcoming 1500 square foot 3-bedroom house completely remodeled in 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 €428
includes taxes & fees
6 Feb - 7 Feb
Welcoming 1500 square foot 3-bedroom house completely remodeled in Southington
2 bedrooms, WiFi, bed sheets

Holiday Home in Berlin

Private Apartment in 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 €251
includes taxes & fees
1 Feb - 2 Feb
Private Apartment in Berlin
3 bedrooms, desk, iron/ironing board, free WiFi

Holiday Home in East Shore

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

Holiday Home in Fair Haven

Gorgeous Waterfront 3 Bedroom, 1.5 Bathroom Unit.
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 €265
includes taxes & fees
2 Feb - 3 Feb
Gorgeous Waterfront 3 Bedroom, 1.5 Bathroom Unit.
Terrace/patio

Holiday Home in Greenport

American Beech in Greenport - Petite King Room 7
9.0 out of 10, Wonderful, (4 reviews)
"We thoroughly enjoyed our stay!"
United States
Parent From The Heart, Inc. E.
The price is €169
includes taxes & fees
1 Feb - 2 Feb
American Beech in Greenport - Petite King Room 7
Dining

Holiday Home in Mill River

Stocked home close to Yale, in Heart of New Haven
9.2 out of 10, Wonderful, (18 reviews)
"Great value very close to university. "
United States
Lawrence
The price is €212
includes taxes & fees
1 Feb - 2 Feb
Stocked home close to Yale, in Heart of New Haven
Smart TV

Holiday Home in Middletown

#29 - Modern 5 Bedroom/2 Bath
9.4 out of 10, Exceptional, (6 reviews)
"Great place! "
United States
Gail R.
The price is €378
includes taxes & fees
31 Jan - 1 Feb
#29 - Modern 5 Bedroom/2 Bath
Terrace/patio

Holiday Home in East Shore

The Jewel of The Cove - Historic Coastal Retreat
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 €421
includes taxes & fees
4 Feb - 5 Feb
The Jewel of The Cove - Historic Coastal Retreat
Marina

Holiday Home in Fair Haven

Gorgeous Waterfront 2 Bedroom 1 Bath Modern Home.
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 €205
includes taxes & fees
2 Feb - 3 Feb
Gorgeous Waterfront 2 Bedroom 1 Bath Modern Home.
Smart TV, fireplace, books, offices

Holiday Home in Old Saybrook

Great Hammcock Getaway, cozy home, hot tub, fire pit, beaches nearby.
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 €425
includes taxes & fees
15 Feb - 16 Feb
Great Hammcock Getaway, cozy home, hot tub, fire pit, beaches nearby.
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 Madison Hotel Reviews

Omni New Haven Hotel at Yale

Omni New Haven Hotel at Yale

10/10 Excellent
"staff was terrific gentleman at the front desk (on 12/31/25) - I don’t recall his name but was super kind"
Josh 1-night trip
Posted 2 days ago
Omni New Haven Hotel at Yale

Find out more about Madison

Madison Holiday Homes information

Number of reviews
133
Accommodation
632 Holiday Homes
Lowest Price
€128
Highest Price
€428