Madison Holiday Rentals

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Check prices for these dates

In two weeks
5 Jun - 7 Jun
In two months
17 Jul - 19 Jul
In three months
14 Aug - 16 Aug
In four months
11 Sept - 13 Sept

Our top choices for Madison holiday rentals

View from property

Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
2.0 star property
East Haddam
9.6 out of 10, Exceptional, (154 reviews)
"I loved the location and the view!"
United States
Gabrielly
The price is HK$1,058
HK$1,577 total
includes taxes & fees
24 Jun - 25 Jun
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
Flat-screen TV

North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.2 out of 10, Wonderful, (18 reviews)
"Great stay & great staff!"
United States
James
The price is HK$2,327
HK$2,659 total
includes taxes & fees
7 Jun - 8 Jun
North Fork Resort
1 bedroom, desk, iron/ironing board, travel cot

1-bedroom cottage with Grove Beach 🏖️ access.

1-bedroom cottage with Grove Beach 🏖️ access.
Clinton
9.6 out of 10, Exceptional, (42 reviews)
"Extremely cozy, comfortable and clean! Really impressed after walking through the door...details of flowers, fruit, water, and coffee and tea. Pleasantly Surprised and would definitely stay again and recommend. Thank you!!"
United States
Kristen B.
The price is HK$931
HK$1,790 total
includes taxes & fees
27 May - 28 May
1-bedroom cottage with Grove Beach 🏖️ access.
Cookware/dishes/utensils

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, (15 reviews)
"wonderful stay - great apartment and location and communication!"
United States
Anonymous traveller
The price is HK$635
HK$1,935 total
includes taxes & fees
25 May - 26 May
Urban Oasis 3BR Parking Washer & Dryer Yale East Rock
Terrace/patio

Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (253 reviews)
"Beautiful property- we would definitely stay there again"
United States
Allison
The price is HK$1,510
HK$2,066 total
includes taxes & fees
31 May - 1 Jun
Cliffside Resort Condominiums
1 bedroom, desk, iron/ironing board, WiFi

One bedroom in United States of America, New Haven

One bedroom in United States of America, New Haven
Dwight
10.0 out of 10, Exceptional, (1 review)
"We enjoyed our stay. The accommodations were clean and spacious and communication was quick and helpful. Would definitely come back!"
United States
Rosanne M.
The price is HK$627
HK$1,463 total
includes taxes & fees
25 May - 26 May
One bedroom in United States of America, New Haven
Interior

Modern Studio Retreat

Modern Studio Retreat
Dwight
The price is HK$1,112
HK$1,770 total
includes taxes & fees
19 Jun - 20 Jun
Modern Studio Retreat
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, (6 reviews)
"Host was very responsive. Property as described. We would stay again! "
United States
john18250
The price is HK$1,646
HK$4,399 total
includes taxes & fees
29 May - 30 May
Rogers Lake House (87) · CT College+Beach+USCGA
TV, offices

Beach Apartment in Woodmont Milford 102

Beach Apartment in Woodmont Milford 102
Milford
The price is HK$733
HK$1,964 total
includes taxes & fees
26 May - 27 May
Beach Apartment in Woodmont Milford 102
Exterior

Cozy Lakefront Tiny House

Cozy Lakefront Tiny House
East Lyme
10.0 out of 10, Exceptional, (3 reviews)
"It was a peaceful and quant "
United States
Patricia M.
The price is HK$1,086
HK$2,144 total
includes taxes & fees
26 May - 27 May
Cozy Lakefront Tiny House
Property grounds

#24 *Serenity* A Lakefront Cottage Retreat

#24 *Serenity* A Lakefront Cottage Retreat
Middletown
9.8 out of 10, Exceptional, (23 reviews)
"The house was cozy and comfortable. The location was great while dropping our son off at Wesleyan University for his sophomore year. The lake was a peaceful place to relax and read."
United States
julia h.
The price is HK$1,417
HK$2,938 total
includes taxes & fees
31 May - 1 Jun
#24 *Serenity* A Lakefront Cottage Retreat
Exterior

All New 1BR with tons of Charm

All New 1BR with tons of Charm
Wallingford Center
9.8 out of 10, Exceptional, (9 reviews)
"Charming, unique, and very comfortable. Would surely stay again. "
United States
David S.
The price is HK$925
HK$2,309 total
includes taxes & fees
25 May - 26 May
All New 1BR with tons of Charm
TV

#35 - Beautiful 3 BR Beach Haven

#35 - Beautiful 3 BR Beach Haven
Old Lyme
10.0 out of 10, Exceptional, (1 review)
"Beautiful property! Just four houses from the beach and a beachfront restaurant. Very comfortable living areas. Well appointed kitchen with in unit washer and dryer. Host was prompt and clear with all communication. Off street parking with room for three vehicles. Too cold to use the outside lounging areas, but they look very nice as well. "
United States
Tim M.
The price is HK$2,507
HK$4,802 total
includes taxes & fees
5 Jun - 6 Jun
#35 - Beautiful 3 BR Beach Haven
Exterior

Angelica’s safe haven @ west haven

Angelica’s safe haven @ west haven
West Haven
10.0 out of 10, Exceptional, (6 reviews)
"We had a great stay. Comfortable home with a large living room. Beds were great. "
United States
Jason V.
The price is HK$1,136
HK$2,637 total
includes taxes & fees
25 May - 26 May
Angelica’s safe haven @ west haven
Interior

Adorable Cottage, 5 min walk to water & town

Adorable Cottage, 5 min walk to water & town
Westbrook Center
9.4 out of 10, Exceptional, (15 reviews)
"Very nice small place to stay by the beach and close to great coffee shop. "
United States
Donovan V.
The price is HK$1,298
HK$3,196 total
includes taxes & fees
26 May - 27 May
Adorable Cottage, 5 min walk to water & town
Dining

2BR Apartment Near Wesleyan 102

2BR Apartment Near Wesleyan 102
Washington Street Historic District
The price is HK$862
HK$2,086 total
includes taxes & fees
26 May - 27 May
2BR Apartment Near Wesleyan 102
1 bedroom, free WiFi, bed sheets

Lakefront Boho Tiny House

Lakefront Boho Tiny House
East Lyme
10.0 out of 10, Exceptional, (5 reviews)
"Every thing was amazing "
United States
Annaliaa C.
The price is HK$991
HK$2,035 total
includes taxes & fees
10 Jun - 11 Jun
Lakefront Boho Tiny House
Property grounds

Family-Friendly Lakeside Cottage with Spectacular Sunset Views Pet-Friendly!

Family-Friendly Lakeside Cottage with Spectacular Sunset Views Pet-Friendly!
Lake Pocotopaug
10.0 out of 10, Exceptional, (16 reviews)
"Clean, quiet, beautiful surroundings and a great host"
United States
Jennifer J.
The price is HK$1,128
HK$2,442 total
includes taxes & fees
4 Jun - 5 Jun
Family-Friendly Lakeside Cottage with Spectacular Sunset Views Pet-Friendly!
TV

All new 1BR apartment with all the features you are looking for

All new 1BR apartment with all the features you are looking for
Wallingford Center
The price is HK$925
HK$2,309 total
includes taxes & fees
25 May - 26 May
All new 1BR apartment with all the features you are looking for
Beach nearby

The Stern at Soundview · Beach+Ocean+Sunrise

The Stern at Soundview · Beach+Ocean+Sunrise
Old Lyme
10.0 out of 10, Exceptional, (3 reviews)
"I had a great experience staying at The Stern! I enjoyed celebrating my weekend there! "
United States
Lylian
The price is HK$980
HK$2,009 total
includes taxes & fees
26 May - 27 May
The Stern at Soundview · Beach+Ocean+Sunrise
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

Best Western Executive Hotel Of New Haven - West Haven

Best Western Executive Hotel Of New Haven - West Haven

10/10 Excellent
"Everything was great besides not having Update body wash / shampoo conditioner tubes for guest , especially big suit rooms you can fit 4 to 5 people and it was just only but a little bars of soap and add more towels and wash cloths tissue in bigger rooms. Everything else was perfect. It was nice and clean, comfortable stay staff was amazing and helpful and kind. Thank you so much for allowing us to stay and to have My Daughter enjoy her graduation night!"
Tiffany 1-night trip
Posted 8 hours ago
Best Western Executive Hotel Of New Haven - West Haven

Find out more about Madison

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

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

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

Frequently asked questions

Are there holiday rentals in Madison?

Yes, there are holiday rentals in Madison close to RJ Julia Booksellers, or you can select a more secluded option if you're looking for a relaxing stay. Nature enthusiasts will enjoy the beaches in Madison. Make sure you have time to check out the aquarium and waterfront during your trip.

What are some of the best holiday rentals that Madison has to offer?

Beautiful, Spacious, Beachfront Home - Perfect for Entertaining Family & Friends: This holiday home rental outside of Madison is located on the beach, and has a balcony, a selection of games and a BBQ 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 that you can cook with friends or family.

How many holiday rentals are there in Madison?

With 32 Expedia holiday rentals, you're guaranteed to find just the right place for your Madison stay.

What’s there to see and do in Madison?

Hammonasset Beach and Meigs Point Nature Center are a couple of scenic spots to enjoy the outdoors, whereas Allis-Bushnell House and Museum is one of the cultural attractions. Hammonasset Beach State Park and North Madison Shopping Center are other places to visit while you're in town.

What’s a holiday rental in Madison like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Madison. Holiday rentals offer extras such as WiFi and washers and dryers so you'll feel just like you're staying in your own home. If you're concerned about a clean environment, a holiday rental can provide a sense of seclusion away from public hotel lifts and busy reception areas while still allowing you the experience of travel. You'll also find more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a great choice for a small group gathering.