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Check prices for these dates

Next weekend
29 Aug - 31 Aug
In two weeks
5 Sept - 7 Sept
In one month
19 Sept - 21 Sept
In two months
17 Oct - 19 Oct

Browse Select Madison Holiday Homes

Our top choices for Madison holiday homes

Cozy 2 bedroom home located minutes from downtown
Interior

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

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

10.0 out of 10, Exceptional, (97)
"We loved our time at White Gate. Very peaceful!"
The price is £1,476
includes taxes & fees
11 Sept - 12 Sept
Historic Inn on a 100 Acre Organic Farm with Lake, Private Pool & Gourmet Food
Cozy Home Near New Haven
Microwave, oven, stovetop, dishwasher

Cozy Home Near New Haven

10.0 out of 10, Exceptional, (1)
"So comfy for the dog and I for a night. Just what we needed!"
The price is £120
includes taxes & fees
9 Sept - 10 Sept
Cozy Home Near New Haven
Modern Beach Home - Waterview, close to restaurants, universities and hospitals
Beach

Modern Beach Home - Waterview, close to restaurants, universities and hospitals

10.0 out of 10, Exceptional, (1)
"The check in process was very easy. The home was airy and bright. My family and I felt the peace and relaxation of the home. The kitchen was large and clean."
Modern Beach Home - Waterview, close to restaurants, universities and hospitals
Beach Front Arts & Crafts House With Gorgeous Views Of The Sound
On the beach, sun-loungers, beach towels

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

10.0 out of 10, Exceptional, (123)
"We had a magical stay in this truly enchanting home the beds were comfortable. The kitchen well equipt for entertaining a large crowd. The fire place and piano were the backdrop for many intimate moments. The gardens were beautiful with azaleas and many perennials. The location directly across from the beach allowed for many walks and playtime together and the waves sung us to sleep at night. We would love to make a new family tradition for visiting here again and again."
Beach Front Arts & Crafts House With Gorgeous Views Of The Sound
Beach Bungalow, walk to beach, private backyard
Fridge, microwave, oven, dishwasher

Beach Bungalow, walk to beach, private backyard

10.0 out of 10, Exceptional, (3)
"The property was perfect for all of us. It was in a quiet neighborhood and great location."
Beach Bungalow, walk to beach, private backyard
Clean, Bright & Private WHOLE HOUSE 4 YOU. 7 Beds
Living area

Clean, Bright & Private WHOLE HOUSE 4 YOU. 7 Beds

10.0 out of 10, Exceptional, (1)
"The space was clean and light, great finishes. The home felt comfortable and was easy to find. Thank you for a wonderful weekend. "
The price is £221
includes taxes & fees
22 Sept - 23 Sept
Clean, Bright & Private WHOLE HOUSE 4 YOU. 7 Beds
Another rental season is coming up.
Outdoor pool

Another rental season is coming up.

10.0 out of 10, Exceptional, (19)
"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.
Charming beach home, complete with pool & cozy guest house!
Interior

Charming beach home, complete with pool & cozy guest house!

9.8 out of 10, Exceptional, (31)
"It was very comfortable and cozy, a very great place to spend with your loved ones, very spacious and had everything we needed to enjoy our stay."
Charming beach home, complete with pool & cozy guest house!
NORTHFORK COTTAGE with POOL & HOT TUB - thru Columbus day
Outdoor spa tub

NORTHFORK COTTAGE with POOL & HOT TUB - thru Columbus day

4.0 star property
9.6 out of 10, Exceptional, (134)
"Loved our stay and will be back"
NORTHFORK COTTAGE with POOL & HOT TUB - thru Columbus day
Exclusive Weekend Summer Sale here Waterfront Beach Home🏖️Hot Tub+Stunning Views
Dining

Exclusive Weekend Summer Sale here Waterfront Beach Home🏖️Hot Tub+Stunning Views

9.8 out of 10, Exceptional, (66)
"We very much enjoyed our stay and were pleasantly surprised by how great the views were from practically every room in the house. Check-in was very simple and there were many nice touches awaiting us at the property. "
Exclusive Weekend Summer Sale here Waterfront Beach Home🏖️Hot Tub+Stunning Views
The Bay Cottage · Rocky Neck Park, Beach & Niantic
Fridge, microwave, oven, stovetop

The Bay Cottage · Rocky Neck Park, Beach & Niantic

2.0 star property
9.0 out of 10, Wonderful, (2)
"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)."
The price is £347
includes taxes & fees
27 Aug - 28 Aug
The Bay Cottage · Rocky Neck Park, Beach & Niantic
Work and Play Special! Extended Stay Discount
Outdoor pool, a heated pool

Work and Play Special! Extended Stay Discount

10.0 out of 10, Exceptional, (49)
"we were pleased to find a beautiful, quiet place to stay and so close to the Vine Street Cafe we could walk"
The price is £1,094
includes taxes & fees
14 Sept - 15 Sept
Work and Play Special! Extended Stay Discount
Aqua Vista
Sun-loungers, beach towels

Aqua Vista

10.0 out of 10, Exceptional, (18)
"This was our second stay at Aqua Vista. We love the property. The house is recently renovated and everything is brand new. It is nicely decorated and very comfortable. It is located close to the beach and center of the town with all of the restaurants. The property manager is a great host. We enjoyed our visit to the fullest."
Aqua Vista
Beachfront Bliss , Inviting 3 bedroom + loft at Hawks Nest Beach!
On the beach

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 Ready 3-bdrm house, Short Walk to Private Beach and Park, Lots of Parking
Beach nearby, sun-loungers, beach towels

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

10.0 out of 10, Exceptional, (40)
"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
Family Gem on Dyer Street
Dining

Family Gem on Dyer Street

The price is £703
includes taxes & fees
25 Aug - 26 Aug
Family Gem on Dyer Street
Newly Renovated, Stylish Peconic Retreat with Private Pool, Lush Grounds,...
Smart TV

Newly Renovated, Stylish Peconic Retreat with Private Pool, Lush Grounds,...

Newly Renovated, Stylish Peconic Retreat with Private Pool, Lush Grounds,...
Historic Coastal Home • Marsh Views • Pet-Friendly
Fridge, microwave, oven, stovetop

Historic Coastal Home • Marsh Views • Pet-Friendly

10.0 out of 10, Exceptional, (1)
"We had a wonderful weekend here!The host was very accommodating with check-in and check-out times. The house was beautiful, spotless and full of character. Lots of space for two families. The yard was really nice and much bigger than it seemed it the photos. We had a really great stay. "
Historic Coastal Home • Marsh Views • Pet-Friendly
Charming 2 bedroom house in Quaint New Suffolk -short walk to New suffolk Beach
Microwave, oven, stovetop, dishwasher

Charming 2 bedroom house in Quaint New Suffolk -short walk to New suffolk Beach

10.0 out of 10, Exceptional, (3)
"We had a wonderful stay. The house is perfect and close to everything. The beach was delightful and ideal for children. "
Charming 2 bedroom house in Quaint New Suffolk -short walk to New suffolk Beach
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
"Desk staff were very professional and knowledgeable of the area. "
Alberto 1-night trip
Posted 14 hours ago
Best Western Executive Hotel Of New Haven - West Haven