Photo by Shannon Willitts

Search Vacation Homes in Madison

  • Plan, book, stay with confidence

    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Next weekend
31 Muh. - 2 Saf.
In two weeks
7 Saf. - 9 Saf.
In one month
21 Saf. - 23 Saf.
In two months
21 Rab. I - 23 Rab. I

Compare 549 Vacation Homes in Madison with updated reviews, rates, and availability.

Enjoy Autumn with us.
Exterior

Enjoy Autumn with us.

10.0 out of 10, Exceptional, (13)
"Ladies weekend. The home was clean and comfortable. We loved how all the kitchen cabinets and drawers were labeled. The host was responsive and accessible The neighborhood was beautiful and close to several of the wineries "
Enjoy Autumn with us.
Cozy Westbrook Vacation Rental - Walk to Beach!
Westbrook Vacation Rental | 3BR | 1.5BA | 1 Step to Enter | 1,350 Sq Ft

Cozy Westbrook Vacation Rental - Walk to Beach!

10.0 out of 10, Exceptional, (11)
"Stayed at this house for a weekend after Christmas. It was great! Perfect location and easy to get everywhere! Would love to stay again."
Cozy Westbrook Vacation Rental - Walk to Beach!
McAngel Haven: 5 mins from Yale
Spaciously Stylish Living Area with Fireplace and Dining View

McAngel Haven: 5 mins from Yale

9.8 out of 10, Exceptional, (9)
"Excellent to had a nice house like that "
The price is SAR 957
SAR 2,126 total
includes taxes & fees
26 Jan - 27 Jan
McAngel Haven: 5 mins from Yale
Amazing Lakefront Property
Dining

Amazing Lakefront Property

9.8 out of 10, Exceptional, (24)
"Absolutely beautiful house! Super clean! Superb setting! Very comfortable! Amazing view! Many amenities! Host very responsive and kind! The property manager quickly responded to our needs. My family and friends loved the spectacular experience and would definitely comeback! "
Amazing Lakefront Property
Walk to the beach at Black Point, Niantic, Ct.
Niantic Bay from end of driveway.

Walk to the beach at Black Point, Niantic, Ct.

9.8 out of 10, Exceptional, (86)
"Wonderful space in a beautiful quiet neighborhood near ocean and cute small town if Niantic"
Walk to the beach at Black Point, Niantic, Ct.
New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.
Exterior

New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.

10.0 out of 10, Exceptional, (9)
"My friends and I have stayed twice now at this house and have had the best time both times! It has everything we could need in the house and we can’t wait to be back again!"
The price is SAR 2,251
SAR 3,200 total
includes taxes & fees
26 Jan - 27 Jan
New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.
The beach is waiting.
Exterior

The beach is waiting.

10.0 out of 10, Exceptional, (25)
"Susan's place was perfect for my family to visit the neighborhood where I grew up! It was clean, comfortable and had everything we needed. It's also a few steps from the beach and the amenities GNB has to offer."
The beach is waiting.
Home on the sound
Room

Home on the sound

8.6 out of 10, Excellent, (7)
"This was a greay stay and the property was really cute and cozy. It is an upstairs portion of a duplex "
Home on the sound
Enjoy a taste of New England in Historic Guilford Ct
Property grounds

Enjoy a taste of New England in Historic Guilford Ct

10.0 out of 10, Exceptional, (9)
"Wonderful property combining original details with modern amenities. Well located near the town green and shops. We would definitely stay here again."
Enjoy a taste of New England in Historic Guilford Ct
Steps to beach! Custom-built house with panoramic ocean views, wrap-around deck.
Raised deck dining and lounging set; additional dining chairs not pictured

Steps to beach! Custom-built house with panoramic ocean views, wrap-around deck.

10.0 out of 10, Exceptional, (42)
"This property is beautiful and the house is spacious and well equipped for a wonderful stay. The host was attentive and easy to contact when it was necessary. Such a fantastic choice for a stay in a delightful town. "
Steps to beach! Custom-built house with panoramic ocean views, wrap-around deck.
Ranch style living at its best with country garden & patio!
Room

Ranch style living at its best with country garden & patio!

9.6 out of 10, Exceptional, (8)
"Host worked with me due to larger dog. Very accurate instructions and all amenities were very good. Will stay here again"
Ranch style living at its best with country garden & patio!
Near Yale with Game Room
Exterior

Near Yale with Game Room

The price is SAR 2,011
SAR 4,295 total
includes taxes & fees
24 Jan - 25 Jan
Near Yale with Game Room
NEW-Another Fun Downtown Location 1st floor
Exterior

NEW-Another Fun Downtown Location 1st floor

2.0 star property
10.0 out of 10, Exceptional, (8)
"Well priced and centrally located in the town. Host was very respectful and helpful. Would definitely book again if I visit southington again."
NEW-Another Fun Downtown Location 1st floor
Walk to Beaches: Sunny East Haven Home w/ Grill
East Haven Vacation Rental | 4BR | 1.5BA | 1,520 Sq Ft | Stairs Required

Walk to Beaches: Sunny East Haven Home w/ Grill

2.0 star property
10.0 out of 10, Exceptional, (3)
"6 of us stayed here for a music festival. The location, fantastic! Ocean views, check. The bedding, the furniture, kitchen supplies....no amenity was overlooked. Happened to meet owner when were checking in. He was great. Couldn't have been more accomodating. Great great place for a few nights or longer. Wush we were here longer. "
Walk to Beaches: Sunny East Haven Home w/ Grill
Family Stays: Middletown, CT
Living room

Family Stays: Middletown, CT

10.0 out of 10, Exceptional, (2)
"We came to stay at Gilbert’s for a quick ski weekend at Powder Ridge. Gilbert was incredibly gracious and accommodating. He was very easy to communicate with, and really went out of his way to make us feel at home. The location is a little loud at night/early morning, as it is very close to a main road. But the property itself was exactly as described. Clean, comfortable, and very welcoming. "
The price is SAR 525
SAR 888 total
includes taxes & fees
12 Feb - 13 Feb
Family Stays: Middletown, CT
Spacious 5-bedroom, 6 bath vacation home just 30 min drive to casinos
Back Patio-Pool, Hot tub, Fireplace, firepit, Bar & TV, Bathroom, Outdoor Shower

Spacious 5-bedroom, 6 bath vacation home just 30 min drive to casinos

10.0 out of 10, Exceptional, (33)
"Spacious, full stocked, amenity filled home with enough room for family members to gather and/or spread out.The game room is perfect for all ages with a variety of choices for your competitive play. Grocery/liquor store and Gillette Castle State Park are minutes away.Beautiful area. "
Spacious 5-bedroom, 6 bath vacation home just 30 min drive to casinos
Oceanfront Oasis Spacious 3-Bedroom, 2-Bath Retreat for 12 Linens Included
Dining area overlooking private beachfront

Oceanfront Oasis Spacious 3-Bedroom, 2-Bath Retreat for 12 Linens Included

9.8 out of 10, Exceptional, (26)
"When my hometown sib couldn't host, we rented here and had our family Thanksgiving! It was great!"
Oceanfront Oasis Spacious 3-Bedroom, 2-Bath Retreat for 12 Linens Included
A TREETOPS Retreat! Sleeps 10-12, perfect for large gatherings. Seasonal POOL!
Exterior image

A TREETOPS Retreat! Sleeps 10-12, perfect for large gatherings. Seasonal POOL!

10.0 out of 10, Exceptional, (24)
"The house is an architectural gem with plenty of space for the family. We enjoyed the fireplace in the evenings."
A TREETOPS Retreat! Sleeps 10-12, perfect for large gatherings. Seasonal POOL!
Historic Inn on a 100 Acre Organic Farm with Lake, Private Pool & Gourmet Food
There's lots to see at the farm!

Historic Inn on a 100 Acre Organic Farm with Lake, Private Pool & Gourmet Food

10.0 out of 10, Exceptional, (87)
"My husband and I stayed at this property with our family members over the New Year's holiday (Dec. 27th to Jan. 3rd). We had the most amazing time. The house has such wonderful space (huge family room/dining area with an super-sized propane fireplace, large kitchen, and family members got their pick of the numerous bedrooms and bathrooms). Its central location to so many other CT towns makes the property even more special and of course, the immense acreage with the plentiful fields and...
Historic Inn on a 100 Acre Organic Farm with Lake, Private Pool & Gourmet Food
Storybook Cottage
Exterior

Storybook Cottage

10.0 out of 10, Exceptional, (1)
"Very charming property, accurate description per listing. Very clean and overall a great stay."
Storybook Cottage
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.
Don't see what you're looking for?
See all available properties in Madison
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other property types in Madison

Writer's Retreat & Explorer's Adventure, S of Rte. 1 Madison!
Room

Writer's Retreat & Explorer's Adventure, S of Rte. 1 Madison!

9.8 out of 10, Exceptional, (25)
"I can not say enough about our stay. Hunter was an amazing host and communication was quick, easy, and made the experience delightful!!! The house is bright and comfy and the view was stunning and relaxing. Every room was perfect from bedroom to living room to kitchen. We wanted for nothing. A quiet getaway to relax was what we were looking for and this was the perfect stay for that. We would love to come back again when we need downtime. This was one of our favorite VRBO rentals ever. Thank...
Writer's Retreat & Explorer's Adventure, S of Rte. 1 Madison!
New Haven Village Suites
Front of property

New Haven Village Suites

3.0 star property
7.6 out of 10, Good, (1996)
"Love this place "
The price is SAR 371
SAR 427 total
includes taxes & fees
30 Jan - 31 Jan
New Haven Village Suites
Cliffside Resort Condominiums
Room

Cliffside Resort Condominiums

3.0 star property
9.0 out of 10, Wonderful, (207)
"Stove it’s not efficient and refrigerator blocked with the corner of wall"
Cliffside Resort Condominiums
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.