A cityscape at dusk with a prominent dome-shaped building, a waterfront, and a circular structure with multiple towers.

Madison Vacation Rentals

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Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Madison vacation rentals

A beach with a house in the background, a clear sky, and a calm sea.

1. Welcoming 1-Bedroom Cottage in Charming Madison is One Mile to Town and Beach!

Welcoming 1-Bedroom Cottage in Charming Madison is One Mile to Town and Beach!
Madison
10.0 out of 10, Exceptional, (2 reviews)
"Cozy cottage was perfect for our long weekend in Madison!"
United States
Samantha D.
The price is ￥25,910
￥58,388 total
includes taxes & fees
Oct 27 - Oct 28
Welcoming 1-Bedroom Cottage in Charming Madison is One Mile to Town and Beach!
A bedroom with a wooden bed, bedside lamps, a sofa, and a TV stand.

2. 1-bedroom cottage with Grove Beach 🏖️ access.

1-bedroom cottage with Grove Beach 🏖️ access.
Clinton
9.6 out of 10, Exceptional, (60 reviews)
"We enjoyed our stay"
United States
JM B.
The price is ￥13,367
￥29,252 total
includes taxes & fees
Oct 11 - Oct 12
1-bedroom cottage with Grove Beach 🏖️ access.
A kitchen with a microwave, stove, and granite countertop. There is a dining area with a sofa and a coffee table.

3. The gardners Cottage 1 mile from long Island Sound - pet friendly

The gardners Cottage 1 mile from long Island Sound - pet friendly
Clinton
9.8 out of 10, Exceptional, (29 reviews)
"Enjoyed our stay - Highly recommend!"
United States
Mary S.
The price is ￥24,913
￥47,356 total
includes taxes & fees
Oct 13 - Oct 14
The gardners Cottage 1 mile from long Island Sound - pet friendly
A cabin with a dining table set for two, a bicycle, and a small porch area.

4. Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
2.5 star property
East Haddam
9.4 out of 10, Exceptional, (200 reviews)
"Great experience and the perfect environment"
United States
Stephanie
The price is ￥22,752
￥33,433 total
includes taxes & fees
Nov 8 - Nov 9
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
A modern kitchen with white cabinets, a microwave, and a large TV displaying a beach scene.

5. Adorable Cottage, 5 min walk to water & town

Adorable Cottage, 5 min walk to water & town
Westbrook Center
9.2 out of 10, Wonderful, (17 reviews)
"Very nice small place to stay by the beach and close to great coffee shop. "
United States
Donovan V.
The price is ￥28,014
￥76,847 total
includes taxes & fees
Oct 15 - Oct 16
Adorable Cottage, 5 min walk to water & town
A dining area with a wooden table, white chairs, a checkered tablecloth, a vase with flowers, and a decorative ceiling light.

6. Adorable Cottage with Cottage porch, walk to water & town

Adorable Cottage with Cottage porch, walk to water & town
Westbrook Center
9.0 out of 10, Wonderful, (8 reviews)
"Very clean and comfortable"
United States
Francine F.
Adorable Cottage with Cottage porch, walk to water & town
A covered patio with a glass table, white metal chairs, a green sofa, and a white metal bench.

7. Historic New England home ,Reunions Beach pass

Historic New England home ,Reunions Beach pass
Guilford
9.2 out of 10, Wonderful, (90 reviews)
"This is a great location, walking distance to the green and other sites. It also worked well for our girls trip of 4 women."
United States
Liz H.
The price is ￥47,454
￥101,710 total
includes taxes & fees
Oct 13 - Oct 14
Historic New England home ,Reunions Beach pass
A living room with a fireplace, a sofa, a coffee table, and a cabinet.

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

Great Hammcock Getaway, cozy home, hot tub, fire pit, beaches nearby.
Old Saybrook
10.0 out of 10, Exceptional, (15 reviews)
"Very clean & comfortable home, great host & location! "
United States
Becky W.
The price is ￥31,636
￥71,260 total
includes taxes & fees
Oct 12 - Oct 13
Great Hammcock Getaway, cozy home, hot tub, fire pit, beaches nearby.
A spacious, well-lit room with a high ceiling, large windows, and a cozy seating area with a sofa and chairs.

9. Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats

Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats
Saybrook Manor
9.8 out of 10, Exceptional, (140 reviews)
"This house comfortably sleeps a lot of guests and has a well equipped kitchen. Everything was very clean. The hosts were very easy to communicate with and very helpful."
United States
Alexis L.
The price is ￥45,556
￥89,008 total
includes taxes & fees
Oct 12 - Oct 13
Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats
A building with a blue entrance marked 'welcome,' a brick facade, and a covered parking area.

10. MS6 Branford | 1 King Bed Smk, Micfridge

MS6 Branford | 1 King Bed Smk, Micfridge
Branford
The price is ￥13,405
￥15,416 total
includes taxes & fees
Nov 8 - Nov 9
MS6 Branford | 1 King Bed Smk, Micfridge
A large, white, multi-story building with a prominent tower and a flag on top.

11. Walk To Goodspeed Opera House!

Walk To Goodspeed Opera House!
East Haddam
9.4 out of 10, Exceptional, (43 reviews)
"Very convenient location with good parking"
United States
Anonymous traveler
The price is ￥21,987
￥38,177 total
includes taxes & fees
Nov 4 - Nov 5
Walk To Goodspeed Opera House!
Terrace/patio

12. Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (295 reviews)
"Great place!"
United States
Christine
The price is ￥26,707
￥48,042 total
includes taxes & fees
Nov 8 - Nov 9
Cliffside Resort Condominiums
A modern house with a deck, outdoor seating, and a fire pit.

13. North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.6 out of 10, Exceptional, (62 reviews)
"Friendly staff. Clean room had everything we needed. Enjoyed our stay!"
United States
Harold
The price is ￥37,882
￥43,280 total
includes taxes & fees
Oct 18 - Oct 19
North Fork Resort
A spacious living area with a wooden floor, a dining table with chairs, a sofa, and a coffee table. There is a kitchen in the background with white cabinets and a wooden countertop.

14. Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown

Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown
Haddam
10.0 out of 10, Exceptional, (38 reviews)
"We had a great stay, very clean and cozy! Our host was very nice and responsive. Great location, would definitely recommend!!!"
United States
Kristy C.
The price is ￥19,750
￥40,448 total
includes taxes & fees
Oct 19 - Oct 20
Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown
A modern living room with a sofa, coffee table, and a TV mounted on the wall.

15. Once the old Schools house now a newly furnished Apartment

Once the old Schools house now a newly furnished Apartment
Wallingford Center
9.2 out of 10, Wonderful, (15 reviews)
"Excellent option for a short stay near the heart of it all in Wallingford."
United States
Jeanette W.
The price is ￥18,644
￥46,563 total
includes taxes & fees
Oct 18 - Oct 19
Once the old Schools house now a newly furnished Apartment
A two-story building with a dark blue facade, a central arched entrance, and a number '43' plaque.

16. All New Studio apartment in center of town

All New Studio apartment in center of town
Wallingford Center
10.0 out of 10, Exceptional, (3 reviews)
"Very clean and comfortable with easy communication with host I recommend this unit to all who want to visit Wallingford or who desire to take the train to ny or Boston etc"
United States
DAVID B.
The price is ￥18,644
￥46,089 total
includes taxes & fees
Oct 16 - Oct 17
All New Studio apartment in center of town
A rocky shoreline with a beach and ocean in the background.

17. The Stern at Soundview · Beach+Ocean+Sunrise

The Stern at Soundview · Beach+Ocean+Sunrise
Old Lyme
8.0 out of 10, Very good, (5 reviews)
"If you are looking for a place to sleep, this place is ok. No place to sit down or put anything down. Just a bed and an old beat up tiny side table. Refrigerator is tiny, needed to be cleaned and defrosted. Stains in the bathroom ceiling tiles and the smell of Marijuana at night. Hot plate and microwave present but did not use. The entryway and stairs were dirty and could use a coat of paint and trim. The beach was the highlight and a very short walk. Definitely not worth the $$$ we paid."
United States
Janine
The price is ￥23,648
￥45,319 total
includes taxes & fees
Oct 12 - Oct 13
The Stern at Soundview · Beach+Ocean+Sunrise
A hotel room with two beds, each with patterned bedding, a bedside table with a lamp, and a wall-mounted phone.

18. Spacious 2 Full Beds Nsmk

Spacious 2 Full Beds Nsmk
Branford
The price is ￥12,789
￥14,708 total
includes taxes & fees
Nov 8 - Nov 9
Spacious 2 Full Beds Nsmk
A hotel with a covered entrance, multiple brick buildings, and a clear sky.

19. Cozy 1 King Bed | Smoking

Cozy 1 King Bed | Smoking
Branford
The price is ￥12,789
￥14,708 total
includes taxes & fees
Nov 8 - Nov 9
Cozy 1 King Bed | Smoking
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

Cambria Hotel New Haven University Area

Cambria Hotel New Haven University Area

10/10 Excellent
"It was very clean and very modern looking we like it a lot"
Dominic 1-night trip
Posted 4 hours ago
Cambria Hotel New Haven University Area

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 vacation rentals in Madison?

Yes, we offer vacation rentals in Madison close to RJ Julia Booksellers, or you can go with a more remote 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 vacation home rentals that Madison has to offer?

New Madison beach house - Ocean front- Great views- booking Summer 2026: This highly rated vacation home rental in Madison is located on the beach and has a balcony, a barbecue grill, and air-conditioning 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. Another good choice for your trip to Madison is Waterfront Estate Home - Pool and Private Beach Pavilion - East.

How many vacation rentals are there in Madison?

With 36 Expedia vacation rentals, you're sure 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 Scranton Memorial Library are other places to visit while you're in town.

What’s a vacation rental in Madison like?

Vacation rentals are privately owned properties where you can stay for a few weeks or just a few days in Madison. Vacation rentals feature extras like WiFi and washers and dryers so you'll have a home away from home. If you're concerned about cleanliness, vacation rentals can offer a sense of privacy away from public hotel elevators and busy front desks while still allowing you to travel. You'll also find more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is an attractive choice for a family getaway.