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Madison vacation rentals

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Top-rated vacation rentals in Madison

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

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Cottage in Guilford

4.93 out of 5 average rating, 264 reviews

Charm + location. Walk to beach, town, & harbor.

We are sharing our "happy place". Cozy, family-friendly cottage has everything you need to enjoy a lovely vacation in a quintessential New England town. Ideally located between Guilford's famous green, gorgeous harbor and town beach, easily walk everywhere. High-season/weekend rate reflected in general view--check for actual. Recommended for groups of up to 4 (5 if with kids). Second bedroom (king) is open to living area-we provide a folding screen for door area and curtain for “passthrough”.

Rental unit in Woodmont

4.97 out of 5 average rating, 552 reviews

Water front studio apartment with fireplace.

This is a beautifully appointed studio apartment located off the patio level of a water front home. Guests enjoy a large private patio over looking gorgeous sweeping views of Long Island Sound. A private entrance and off street parking. The amazing views and amenities make this space the perfect romantic getaway! Close to I95 and Metro North railroad. Ten minutes to great dining in downtown Milford. A true waterfront oasis! Come and experience this beautiful retreat! You won't be disappointed!

Rental unit in Guilford

4.99 out of 5 average rating, 269 reviews

Guilford Guest House- private studio apartment

Quintessential New England shoreline town. Arrive by Car, Train or by boat and walk from the marina to our guest house. (Inquire) Walk to the Guilford Green, Town Dock, Jacobs Beach along with over a dozen restaurants, pubs, coffee shops, gift & clothing shops. Hiking trails . Please review my extensive guide book of Guilford and the surrounding areas. Walking access to the Shoreline East train to surrounding Local towns or transfer to Metro north and Amtrak to NYC & Boston all without a car.

Cottage in Westbrook

4.88 out of 5 average rating, 127 reviews

Peaceful Riverfront Cottage w/Dock, Walk to Beach

This lovely Cottage sits directly on the Patchogue River with scenic views of the river and marshlands from every room and just a 1/4 mile walk or bike to the Beach. Private, but close to so much, it’s Perfect for a Romantic Getaway, or a long Vacation. Outside, you can enjoy the breeze from the Riverfront Deck, Sun Bathe, Crab or Fish on the Lower Dock, watch the Eagles fly by, or wander about the wooded property. Bring or rent a Kayak and paddle down the river right to the Long Island Sound.

Bungalow in Woodmont

4.98 out of 5 average rating, 268 reviews

Fall Sale!Beach Bungalow |Pet-friendly|WalktoBeach

Welcome to the Beach Bungalow, completely remodeled to the studs in '21! This Woodmont by the Sea home is a 3 block stroll to Anchor Beach & the walkway along beautiful Beach Ave. The home offers a modern kitchen, dining for 6, private back porch & outdoor shower. This +775sf bungalow has a driveway & on-street pkg. It's located in a charming coastal town, walking distance to restaurants, grocery store & Robert Treat Farm and is 2 mi to I95, 10 mi to Yale/New Haven...and mins to breweries.

Guesthouse in Portland

4.99 out of 5 average rating, 149 reviews

Guesthouse Farm Stay

Come stay with us on our working farm. Relax and take in our beautiful 12-acre property while sitting on the back deck, overlooking pastures. Or for a more interactive experience, join us on a farm tour during our morning and evening farm chores. Our farm was established in 1739 with a rich history in agriculture and livestock. Our cottage is studio-style with an open bedroom, living room, and dining area. There is a kitchette and bathroom with a shower for your convenience.

Home in Haddam

5 out of 5 average rating, 104 reviews

Cozy Comforts!

Keep it simple at this peaceful and centrally-located place. Completely open concept and fully renovated. Country living yet just minutes to downtown Middletown and Wesleyan University. Come stay at our home away from home! We are about 20-25 min from the shoreline or travel in the other direction and you’ll be in our state’s capital, Hartford. We are only about 10-15 min from Wesleyan and downtown Middletown for shopping and great restaurants! You don’t want to miss this one!

Rental unit in Old Saybrook Center

4.96 out of 5 average rating, 120 reviews

Convenient and Cute in Downtown Old Saybrook

Welcome to Old Saybrook! Our apartment sits over our garage and is attached to our primary residence. It is conveniently located within walking distance to Main Street, the beach, local parks, and other town attractions. We have recently made many upgrades to the property and we're ready for guests! We look forward to sharing our home with you! **PETS: DOGS ALLOWED BY PRE-APPROVAL ONLY and ADDITIONAL $25 PET CLEANING FEE. Please see House Rules for more info.

Guest suite in Wallingford

5 out of 5 average rating, 544 reviews

Wintergreen Gardens Suite @ William Becroft House

LGBTQ friendly. Our 1915 Arts & Crafts bungalow's spacious in-law suite offers driveway parking, private entrance, sunroom, king bedroom, en-suite bath, kitchenette w/fridge, micro, coffee maker, toaster. Relax in bed with 40" HDTV with Amazon Prime, HBO Max, Netflix, premium cable. Enjoy private gardens to sun, read a book or cup of coffee. Short drive to 4 Vineyards, Theater and the train station.

Guesthouse in Mystic

4.98 out of 5 average rating, 599 reviews

Gorgeous Waterfront Getaway

Perfect getaway from the city for couples wanting peace and tranquility and stunning views. A beautiful waterfront one bedroom guesthouse, one and one-half miles from downtown Mystic CT. Beautifully decorated with art and antiques. Kitchenette, full bath and loft bedroom. Queen bed. Air conditioning and heated. Belgian linen bedding! Private patio. Dock. Kayak/Canoe rentals close by. Internet.

Cottage in Madison

5 out of 5 average rating, 102 reviews

Shabby Chic Retreat

Mon thru Thru $200/night. Fri -Sun $250/night. Thinking ahead…the shoreline towns are great for magical Christmas experiences and unique boutique shopping. When in CT we stay in the studio apt on the lower level of the cottage. It has a separate entrance. PLEASE NOTE: The pet fee is $25/night, per pet (not per stay)

Guest suite in Essex

4.96 out of 5 average rating, 103 reviews

The Nest

Our warm and inviting studio apartment with bright and cheery decor offers a cozy get away any time of year. Nestled in a peaceful country neighborhood with endless hiking trails, beaches, and cozy villages nearby. The Nest offers a comfortable and convenient place to stay while enjoying the surrounding area.

Vacation rentals for every style

Get the amount of space that is right for you

Cottages

Quaint homes, peaceful surroundings

Houses

A space thats all yours, with room for everyone

Hotels

Stylish accommodations and amenities

Popular amenities for Madison vacation rentals

Laptop-friendly workspace

Stay near Madison's top sights

Hammonasset Beach State Park173 locals recommend

Clinton Crossing Premium Outlets109 locals recommend

Chamard Vineyards Bistro63 locals recommend

Lobster Landing39 locals recommend

RJ Julia Booksellers35 locals recommend

The Place Restaurant31 locals recommend

Madison beach vacation rentals

Home in East Haven

4.96 out of 5 average rating, 132 reviews

The Breakaway - a waterfront gem.

Home in Shelter Island

4.95 out of 5 average rating, 223 reviews

Huge Island Getaway Pool HotTub Walk To Beach

Rental unit in Branford

4.97 out of 5 average rating, 103 reviews

Ridgeview Suite at Stony Creek Depot

Home in Madison

5 out of 5 average rating, 41 reviews

Writer's Retreat & Explorer's Adventure!

Home in North Fork

4.95 out of 5 average rating, 334 reviews

The Sandpiper

Home in East Lyme

4.97 out of 5 average rating, 122 reviews

Walk to the beach at Black Point, Niantic, Ct

Cottage in Milford

4.99 out of 5 average rating, 105 reviews

Modern Cottage, Walk 2 Beach & Tyde Wedding Venue

Home in Milford

4.99 out of 5 average rating, 113 reviews

Serene Waterfront Retreat - 400 ft Private Beach!

Other great vacation rentals in Madison

Barn in Madison

4.96 out of 5 average rating, 46 reviews

Cozy Restored barn near beaches

Barn in Guilford

4.95 out of 5 average rating, 87 reviews

Pristine Carriage House Apartment Downtown

Home in Madison

5 out of 5 average rating, 13 reviews

Beach Home & Garden Paradise

Rental unit in Guilford

4.97 out of 5 average rating, 60 reviews

Cozy Private Lake Q Retreat

Home in Clinton

5 out of 5 average rating, 6 reviews

Boulder Lake House Retreat

Cottage in Madison

4.92 out of 5 average rating, 26 reviews

Adorable cottage close to beaches and downtown

Home in Madison

4.87 out of 5 average rating, 23 reviews

Historic Beachside Glamour

Guest suite in Guilford

4.95 out of 5 average rating, 37 reviews

Guilford studio apartment, steps from the Green

Quick stats about vacation rentals in Madison

Total rentals
130 properties
Total number of reviews
3.9K reviews
Family-friendly rentals
80 properties are a good fit for families
Pet-friendly rentals
40 properties allow pets
Rentals with a pool
10 properties have a pool
Rentals with dedicated workspaces
40 properties have a dedicated workspace

Frequently Asked Questions

Are there vacation rentals with a dedicated workspace in Madison?
Yes! Work meets play with ease at over 40 vacation rentals in Madison featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there pet-friendly vacation rentals in Madison?
Four-legged friends are welcome in Madison. Choose from more than 40 vacation rentals for guests traveling with pets.
How much does it cost to stay in cottage rentals in Madison?
Experience the best of Madison with our cottage rentals, starting at about $120 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do house rentals in Madison have a bbq area?
Absolutely! We offer over 40 house rentals with a bbq area in Madison. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Madison have self check-in?
Absolutely! We offer over 20 house rentals with self check-in in Madison. Enjoy a tailored experience with all the comforts you desire.
Are there Madison vacation rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 10 vacation homes with pools in Madison, available on Airbnb. Make a splash and soak up the sun in style!
Are there family-friendly house rentals in Madison?
Madison has more than 50 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
What are the most popular amenities for House Rentals in Madison?
Enhance your stay in our House Rentals with the most popular amenities: over 20 homes with self check-in, over 40 homes with a bbq area, and more. Indulge in the ultimate retreat, tailored to your preferences.

Destinations to explore