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Vacation Homes in Madison

Cozy 2 bedroom home located minutes from downtown

9.6 out of 10, Exceptional, (29)
"Perfect stay for the Yale-Harvard game. "
Cozy 2 bedroom home located minutes from downtown

NORTHFORK COTTAGE with POOL & HOT TUB - thru Columbus day

4.0 star property
9.6 out of 10, Exceptional, (133)
"Loved our stay and will be back"
NORTHFORK COTTAGE with POOL & HOT TUB - thru Columbus day

Cozy 3 bedroom minutes from Yale and the beach

7.0 out of 10, Good, (2)
"The inside was very clean, the back patio/garden area is cute, but the pool was green by day two. Overall we enjoyed our time here"
Cozy 3 bedroom minutes from Yale and the beach

Beach Ready 3-bdrm house, Short Walk to Private Beach and Park, Lots of Parking

10.0 out of 10, Exceptional, (38)
"Very clean well kept property near beach - host very welcoming and receptive. Enjoyed our stay!"
Beach Ready 3-bdrm house, Short Walk to Private Beach and Park, Lots of Parking

Another rental season is coming up.

10.0 out of 10, Exceptional, (18)
"Absolutely beautiful home with everything you need for an enjoyable vacation. The host was a pleasure to work with making sure we were comfortable with our accommodations. Definitely a great place to stay. "
Another rental season is coming up.

Grammy's Lake House w/ Private Waterfront Access

9.4 out of 10, Exceptional, (13)
"Very comfortable rockers and Adirondack chairs make it easy to relax and enjoy the lake view. Our bed was comfortable, and Nile supplied all we needed with linens and soaps. We appreciated all the space and large dining table. Lake is beautiful. Very enjoyable stay. Exceptional communication with our host. "
Grammy's Lake House w/ Private Waterfront Access

Work and Play Special! Extended Stay Discount

10.0 out of 10, Exceptional, (48)
"We had a lovely time at Cottage Green. Ingrid was a lovely owner and was very easy to communicate with!"
$1,365 nightly
The price is $1,560
Sep 4 - Sep 5
Total includes taxes and fees
Work and Play Special! Extended Stay Discount

The SandPiper

9.8 out of 10, Exceptional, (24)
"My friends and I stayed here for a night after a wedding. It was the perfect place to stay after a long day. Host was kind and helpful with anything I needed! "
The SandPiper

American Beech in Greenport - Petite King Room 7

8.8 out of 10, Excellent, (3)
"We thoroughly enjoyed our stay!"
$313 nightly
The price is $358
Aug 13 - Aug 14
Total includes taxes and fees
American Beech in Greenport - Petite King Room 7

Beachfront Bliss , Inviting 3 bedroom + loft at Hawks Nest Beach!

4.8 out of 10, (3)
"Overall, my girlfriends and I had a good stay at this accommodation. Transparently, there were some hiccups in communication between the property manager and I in the week leading up to our trip that were not clearly stated in the home's description prior to us booking our stay, however, I felt that they were able to address my concerns and came up with solutions that felt satisfactory to my group and I. The property manager was overall understanding and receptive to my feedback through our...
Beachfront Bliss , Inviting 3 bedroom + loft at Hawks Nest Beach!

Beach Front Arts & Crafts House With Gorgeous Views Of The Sound

10.0 out of 10, Exceptional, (121)
"Beautiful historic home, views of the Sound, pleasant walking neighborhood."
Beach Front Arts & Crafts House With Gorgeous Views Of The Sound

New hot tub & outdoor TV! 3 bedroom apt dwntn Middletown, across from Wesleyan

2.0 star property
10.0 out of 10, Exceptional, (6)
"Everything about our stay at this property was great. Communication, check-in, cleanliness, etc. The location is directly across the street from Wesleyan University which made my son's visit all the better. I will definately stay here again."
New hot tub & outdoor TV! 3 bedroom apt dwntn Middletown, across from Wesleyan

adorable ranch in beach community

10.0 out of 10, Exceptional, (45)
"Close to the shore and the heart of Old Saybrook. The house is very comfortable."
$571 nightly
The price is $646
Aug 13 - Aug 14
Total includes taxes and fees
adorable ranch in beach community

Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub

10.0 out of 10, Exceptional, (136)
"Perfect location for a get-away! Beautiful location on the water. The cottage was cozy & had everything we needed. Very clean. Lots to do in the area. Host was very nice We had a great time and will absolutely be back! "
Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub

Waterfront House with picture-perfect views from all 3 levels.

9.6 out of 10, Exceptional, (92)
"It was a very nice stay. Sound of the ocean was calming. We would go back. "
Waterfront House with picture-perfect views from all 3 levels.

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

10.0 out of 10, Exceptional, (92)
"We loved our time at White Gate. Very peaceful!"
Historic Inn on a 100 Acre Organic Farm with Lake, Private Pool & Gourmet Food

The Beach Nest-Lux Cottage Steps to the Beach

9.8 out of 10, Exceptional, (6)
"Quick weekend stay as we needed to be in the area for a soccer tournament. The house was super clean and had everything we needed. Would definitely stay again. "
The Beach Nest-Lux Cottage Steps to the Beach

Crescent Beach Cottage - Vacation or Academic Rental

9.2 out of 10, Wonderful, (15)
"We had a great time. Perfect location. There were some concerning things about the property, but nothing major. Will reach out to the renter privately."
Crescent Beach Cottage - Vacation or Academic Rental

The Beach House - Old Lyme

10.0 out of 10, Exceptional, (17)
"Exquisite botanical garden!"
The Beach House - Old Lyme

Gorgeous 4BR Beach House with Private Beach Access.

9.8 out of 10, Exceptional, (74)
"We loved our stay at this beautiful cottage. The entire experience was very smooth, from pre-check in to getting there and even offers to help with anything we needed in our stayThe cottage is very cozy and well-cared for. The rooms are comfortable and the Internet fast. There is a lot to do in the area, with New Haven nearby and many good restaurants."
Gorgeous 4BR Beach House with Private Beach Access.
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