Apartment vacation rentals in Madison

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Top-rated apartment rentals in Madison

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Guest favorite

Apartment in Burlington

4.85 out of 5 average rating, 108 reviews

Charming apartment with breathtaking view!

The guest apartment ( FULLY RENOVATED FINISHED BASEMENT) is an addition to our luxurious home. A 2 bedroom apartment with one king sized bed, Queen sized bed and a plush leather pull out sofa. Pool l table. Large in ground pool, 2 cabana beds, fire pit and dining table. Pool and gated backyard is exclusive to guests. We include netflix, hulu and hbo max. THE (HEATED) POOL IS OPENED IN MAY AND CLOSED LATE SEPTEMBER. The pool is cleaned daily in the morning. The pool is exclusive to guests.

Guest favorite

Apartment in Mystic

4.92 out of 5 average rating, 172 reviews

Stylish Downtown Mystic Apt.

Experience the unique charm of Mystic in this fully-renovated and centrally-located apartment featuring 2 bedrooms and 1 bathroom in the heart of downtown. Located a few blocks from the Mystic train station and steps from dozens of restaurants, shops, and world-class attractions like Mystic Seaport and Mystic Aquarium, this property offers the perfect combo of space, style and convenience. After exploring our beautiful coastal town, you'll look forward to relaxing at your home-away-from-home.

Superhost

Apartment in Wooster Square

4.84 out of 5 average rating, 131 reviews

Lovely 2BR by Wooster Sq.- great neighborhood!

Welcome to New Haven, CT! Come stay in our beautiful apartment located walking distance to Wooster Square. It's close to some great restaurants, parks, nightlife, and all the great landmarks in the area! Amenities include a full kitchen with Keurig/K-cups, Wifi, Smart Roku TV with apps, full bath with towels, shampoos/lotions, laundry room, and workspace with desk to name a few. Located in a quiet neighborhood, this space is perfect for anyone traveling, studying, working remotely, etc.

Top guest favorite

Apartment in Sag Harbor

4.98 out of 5 average rating, 172 reviews

Updated apartment in historic village home

Quiet updated apartment close to Main St, boats and beaches. This second floor apartment has a private entrance and allows use of the front yard. Our home was built in 1880 but has just been renovated for a modern beach bungalow feel. The location is the perfect balance of a quiet neighborhood and close proximity to Marine Park, shops, restaurants, the Hampton Jitney and nightlife. The center of main street is less than a quarter mile from the apartment (4 minutes on foot). Walk to all!

Superhost

Apartment in Downtown Stamford

4.86 out of 5 average rating, 131 reviews

Modern Luxe 1BR Apt in Downtown Stamford

This super clean cozy space will be your home away from home. Located in the heart of Downtown Stamford within walking distance to shopping area, restaurants and bars. 3 minutes from the I-95 and 4 minutes from the Metro North Stamford Station with easy access to NYC. This luxury apartment has all the essentials you’ll need to rest, relax and rejuvenate. Enjoy seamless check in with key lock, fast internet, and major essentials. You’ll have access to a fitness center and rooftop.

Guest favorite

Apartment in Groton

4.85 out of 5 average rating, 424 reviews

⚓ Downtown Mystic- Top Location, Parking, WiFi, AC

Super walkable location with free parking spot and Smart TVs! Enjoy water views of the Mystic River while you relax on the front porch and watch the boats go by. Located right on Water Street, this apartment is literally steps away from some of the best restaurants and attractions in Downtown Mystic. Comfortably furnished to accommodate up to 6 guests with linens, towels, cookware, bathroom amenities and coffee/ tea, and off-street parking included!

Top guest favorite

Apartment in Fairfield

4.97 out of 5 average rating, 119 reviews

Sunny Fairfield Studio Apartment

Enjoy this sunny, newly-renovated, modern Fairfield studio apartment, located in the carriage building of a historic early 1900's house. Great for an individual, couple, or family. Well situated, a short drive to Sacred Heart & Fairfield Universities, downtown Fairfield and the beach, Silverman's Farm and other Easton farms for apple picking, petting zoos, and the like, and Fairfield Metro Station for a 1 hour train ride to NYC.

Guest favorite

Apartment in Montauk

4.86 out of 5 average rating, 111 reviews

Recharge at our Renovated ocean front unit

Looking for a relaxing weekend to recharge on the beach? Then this newly renovated, bohemian-chic, apartment is perfect for you. Imagine waking up every morning to beautiful unobstructed ocean views and ending your night with a drink in hand watching the sunset. If you’re lucky, you might see some whales or dolphins breaching in the water right off our private beach. We would love to host you for your Montauk beach getaway.

Guest favorite

Apartment in Mystic

4.89 out of 5 average rating, 113 reviews

Downtown Mystic, Private Luxury 2BR w Free Parking

Recently renovated and perfectly located! A private two-bedroom apartment on a private street in central Historic Mystic, CT! Free parking on premises for guests Park your car and never use it - Close walk to multiple famous attractions! - Mystic Pizza - Famed Drawbridge - Seaport Museum - Main Street Driving distance to even more - Mystic Aquarium, beaches, casinos, golf courses, Olde Mistick Village, and more!

Top guest favorite

Apartment in North Fork

4.96 out of 5 average rating, 143 reviews

Upscale Newly Constructed Apartment

Upscale 2- story building offers 3 bedrooms, 2 baths spacious apartment in the heart of Greenport. A vaulted ceiling in the great room (kitchen, dining & living room) with large windows and hardwood floors with plenty of natural light. Utilities included. CAC, Laundry. Less than a mile to a public beach, public transportation, restaurants, shops and Mitchell park. Off street parking for 2-3 cars.

Guest favorite

Apartment in Shelter Island Heights

4.91 out of 5 average rating, 245 reviews

Squire Chase House

Wide open loft like space in the heart of the Heights walking distance to North ferry and Marie Eiffel market Many antiques including 1930s leather club chairs and a wonderful 1850 Swedish gustavian sofa in the living room many original pieces of art work Note :the bath tub in the master bedroom is for decoration only Shelter Island license B Zone

Guest favorite

Apartment in North Fork

4.82 out of 5 average rating, 119 reviews

House on First

This beautiful upstairs apartment is 2 blocks from the charming Village of Greenport. It’s walking distance to many fine restaurants, beautiful beaches, antique carousel in Mitchell Park and ferry to Shelter Island. There’s a deck upstairs you can have your morning coffee before you head out on your next adventure!