Madison Vacation Rentals

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Browse Select Madison Vacation Homes

Historic Inn on a 100 Acre Organic Farm with Lake, Private Pool & Gourmet Food
View from property
Historic Inn on a 100 Acre Organic Farm with Lake, Private Pool & Gourmet Food
10.0 out of 10, Exceptional, (81)
"Whitegate Farm is beautiful. The staff were super friendly and always helpful. The food is delicious! Highly recommend this place for group outings "
Historic Inn on a 100 Acre Organic Farm with Lake, Private Pool & Gourmet Food
Gorgeous Waterfront 3 Bedroom, 1.5 Bathroom Unit.
Smart TV
Gorgeous Waterfront 3 Bedroom, 1.5 Bathroom Unit.
9.4 out of 10, Exceptional, (10)
"Beautiful condo as advertised, great communication."
The price is CA $205
CA $388 total
includes taxes & fees
Sep 30 - Oct 1
Gorgeous Waterfront 3 Bedroom, 1.5 Bathroom Unit.
Oceanfront Oasis Spacious 3-Bedroom, 2-Bath Retreat for 12 Linens Included
View from property
Oceanfront Oasis Spacious 3-Bedroom, 2-Bath Retreat for 12 Linens Included
9.8 out of 10, Exceptional, (24)
"We booked late in summer and spent 2 nights on beach road when we should have stayed longer. Fantastic location, great neighborhood, clean and comfortable beach house, my wife and I very much enjoyed the house and the shore. Can’t wait to book again!"
The price is CA $506
CA $997 total
includes taxes & fees
Oct 13 - Oct 14
Oceanfront Oasis Spacious 3-Bedroom, 2-Bath Retreat for 12 Linens Included
Waterfront Beach House
Terrace/patio
Waterfront Beach House
9.6 out of 10, Exceptional, (35)
"Beautiful home in great location. Worked perfectly for our family. House was in amazing shape, outdoor patio was awesome! As prior reviews have said, make sure you have water shoes, the water for the first 5-10 ft is very rocky. But overall everything was amazing"
Waterfront Beach House
Year-Round Waterview 4 Beds, 2 Baths, Sleeps 13 with Linens & Towels Included
Beach nearby, sun loungers, beach towels
Year-Round Waterview 4 Beds, 2 Baths, Sleeps 13 with Linens & Towels Included
9.2 out of 10, Wonderful, (80)
"We enjoyed our long weekend stay at the Count House. Its location was perfect ... easy beach access, close to the highway, etc. Everything we needed was supplied for us to enjoy the beach, cook our meals, or play games. There was only one full-size kayak with paddle and the paddle board paddle was broken (but we used it by kneeling on the board!). We would definitely return."
The price is CA $202
CA $582 total
includes taxes & fees
Sep 29 - Sep 30
Year-Round Waterview 4 Beds, 2 Baths, Sleeps 13 with Linens & Towels Included
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, (111)
"Had a quick work trip and wish we stayed longer! "
Beach Front Arts & Crafts House With Gorgeous Views Of The Sound
Historic Essex Home w/ Large Yard Near Downtown!
TV
Historic Essex Home w/ Large Yard Near Downtown!
9.8 out of 10, Exceptional, (39)
"All bedrooms up were difficult with luggage. Fully equipped for an extended stay would be convenient. Very close to marina and shopping."
Historic Essex Home w/ Large Yard Near Downtown!
Riverview Grandeur Tranquility & Luxury Essex CT
Fridge, microwave, oven, stovetop
Riverview Grandeur Tranquility & Luxury Essex CT
2.0 star property
9.6 out of 10, Exceptional, (4)
"This property is well maintained, conveniently located, has superb amenities and has beautiful views of the CT river. I recommend it highly and without qualification,"
Riverview Grandeur Tranquility & Luxury Essex CT
Sunny East Haven Home w/ Grill: Walk to Beaches!
Beach nearby
Sunny East Haven Home w/ Grill: Walk to Beaches!
2.0 star property
10.0 out of 10, Exceptional, (1)
Sunny East Haven Home w/ Grill: Walk to Beaches!
Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub
Property grounds
Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub
10.0 out of 10, Exceptional, (123)
"Our stay was incredible! The property was gorgeous- even with the home owners on property we barely saw them. We had full, private access to the backyard space- beach, pool, hot tub, fire pit, etc- all to ourselves. The property was clean and inviting and we will definitely go back. Everyone was so friendly and the area is picturesque. "
Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub
Seaside Serenity: Relaxation by Jacob's Beach
TV, offices
Seaside Serenity: Relaxation by Jacob's Beach
9.2 out of 10, Wonderful, (28)
"Very close to the beach (with large playground and splash pad) and a 15 minute walk to town. Comfy beds with nice linens and plenty of towels. Included beach towels and chairs as well as a beach wagon. Host very responsive. Have stayed there before and will stay there again! "
Seaside Serenity: Relaxation by Jacob's Beach
Beautiful, Spacious, Beachfront Home - Perfect for Entertaining Family & Friends
Interior
Beautiful, Spacious, Beachfront Home - Perfect for Entertaining Family & Friends
10.0 out of 10, Exceptional, (45)
"This house is beautiful and has everything you need, including a gorgeous view of the Sound. All communication was swift and easy. My family built some wonderful memories here this week!"
Beautiful, Spacious, Beachfront Home - Perfect for Entertaining Family & Friends
OCEAN/BEACH FRONT, HUGE YARD, SUNSET VIEW
View from property
OCEAN/BEACH FRONT, HUGE YARD, SUNSET VIEW
9.4 out of 10, Exceptional, (30)
"Amazing house on the beach with tons of space for fun!!! We loved being right on the water. The kids found crabs and fished with some of the locals. Would definitely rent this place again!!"
OCEAN/BEACH FRONT, HUGE YARD, SUNSET VIEW
Waterfront House with picture-perfect views from all 3 levels.
Interior
Waterfront House with picture-perfect views from all 3 levels.
9.6 out of 10, Exceptional, (72)
"It was lovely falling asleep to sound of waves every night. The house was comfortable and clean. The owners, Carolyn and Jon, were responsive and helpful. We had a great week."
Waterfront House with picture-perfect views from all 3 levels.
Cozy newly remodeled home close to major amenities in Connecticut a
Private kitchen
Cozy newly remodeled home close to major amenities in Connecticut a
8.2 out of 10, Very good, (15)
"We came to ct from South Carolina for my nieces wedding. E didn’t know what to expect. When we got there we were pleasantly surprised. The house was clean had a little fenced in patio. Check in was easy. Had easy access to the highway. The only thing I wish was that it had a first floor bathroom. But the house was perfect. Thank you. "
Cozy newly remodeled home close to major amenities in Connecticut a
New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.
Fridge, microwave, oven, stovetop
New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.
10.0 out of 10, Exceptional, (5)
"To say that the property was in pristine condition and impeccably designed and decorated would be understatements. Everything was perfect and if we could have stayed in this luxurious home longer, we would have. The property was a perfect launching point for our visit to Powder Ridge for mountain biking and to visit other nearby sites in the beautiful area. The host responded to inquiries without delay and was a pleasure to interact with. We highly recommend without hesitation!"
The price is CA $809
CA $1,150 total
includes taxes & fees
Sep 27 - Sep 28
New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.
Lakefront Home, Close to Mt Southington!
Fridge, microwave, stovetop, dishwasher
Lakefront Home, Close to Mt Southington!
10.0 out of 10, Exceptional, (12)
"Staff very much enjoyed the atmosphere after long days of work. Wonderful Ownership. Thank you so much Susan!"
Lakefront Home, Close to Mt Southington!
Grammy's Lake House w/ Private Waterfront Access
Grammy's Lake House w/ Private Waterfront Access
10.0 out of 10, Exceptional, (7)
"Had a very good time We enjoyed the front porch"
Grammy's Lake House w/ Private Waterfront Access
NEW! Seaside Beach Haven with a private beach!
Property grounds
NEW! Seaside Beach Haven with a private beach!
10.0 out of 10, Exceptional, (9)
"It was absolutely gorgeous. We truly enjoyed our stay. 5 ⭐️"
NEW! Seaside Beach Haven with a private beach!
Heavenly Home in New Haven
Smart TV, printers
Heavenly Home in New Haven
8.8 out of 10, Excellent, (15)
"The property was prepared well and we enjoyed our stay. Thanks"
The price is CA $641
CA $828 total
includes taxes & fees
Sep 27 - Sep 28
Heavenly Home in New Haven
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Other property types in Madison

Writer's Retreat & Explorer's Adventure, S of Rte. 1 Madison!
Smart TV, video games, books, stereo
Writer's Retreat & Explorer's Adventure, S of Rte. 1 Madison!
9.8 out of 10, Exceptional, (22)
"We had a wonderful 3-night stay at this little river-front house. What a perfect home base for our family vacation. I asked the owner (Hunter) ahead of booking if they happened to have a pack n play for our 2-year old (he messaged back very quickly that they did!), and we were so appreciative to walk in and find that not only did they set up all of the baby gates, outlet plugs, toilet lock, pack n play for us, but they even had age-appropriate toys and books out for our use! It all was far...
Writer's Retreat & Explorer's Adventure, S of Rte. 1 Madison!
New Haven Village Suites
Fridge, microwave, coffee/tea maker, cookware/dishes/utensils
New Haven Village Suites
3.0 star property
7.6 out of 10, Good, (1926)
"Excellent! Best kept secret in New Haven. My room was spacious. Lobby was beautiful and had coffee and breakfast. I would stay again, but you must have a car."
The price is CA $134
CA $154 total
includes taxes & fees
Oct 27 - Oct 28
New Haven Village Suites
Cliffside Resort Condominiums
Beach nearby
Cliffside Resort Condominiums
3.0 star property
9.0 out of 10, Wonderful, (202)
"Beautiful condo Convienent Spacious Only issue check in 4 pm Checkout at 10 am "
The price is CA $421
CA $539 total
includes taxes & fees
Sep 29 - Sep 30
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.