Apartment holiday rentals in Madison

Modern Carriage House Near Beach - Deck + Fire Pit

Come stay on the closest property to Hammonasset Beach State Park in all of Madison! Just 1 mile and your feet are on 2 miles of white sandy beach to explore and enjoy. This fully renovated carriage house is nestled on a grassy 1.5-acre property near town. Enjoy your own private entrance, full kitchen, sunny deck, fire pit, and outdoor dining space. Located across from the Greenway Trail and close to shops, restaurants. Ideal for couples or small families looking for a relaxing coastal getaway!

Private apartment in historic Old Lyme mansion

3rd floor apartment in Ludington House, a historic home centrally located in the charming village of Old Lyme. 3 bedrooms (2 queen, and one with two twin beds/trundle), 2 full bathrooms. Close to restaurants, beaches, art galleries and museum. Person booking the apartment must be one of the guests staying. We do not allow guests that are not part of the reservation to visit the property during your stay. No loud late nights. Rental does not include access to lower floors, billiard room, porch.

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!

Bright 1 BR Apt Steps From Yale

Enjoy a bright and cozy 1 bedroom apartment just 2 blocks from the Yale campus and The Shops at Yale. Located in a 3 unit brick building, designated as a property on The National Register of Historic Places, this small renovated 2nd floor apartment maintains the characteristics of the building's original design, while providing all amenities needed for a comfortable stay. Convenient free off street parking provided. Great shops, restaurants, nightlife, and museums can all be accessed by foot.

The Pearl, New Haven

Amazing hidden luxury experience along the Quinnipiac River in a historic mid-19th century property. Enjoy the scenic river and sunset views, soak in our stunner claw-foot tub, recharge in the sunlit living room, work in the dining alcove, or relax by the bay windows with your favorite drink. NO KITCHEN, but we have a coffee maker, tea kettle, toaster oven, microwave, fridge, plates, and cutlery. We are 15 mins drive from Yale, 2 mins walk to the downtown bus, and easy cycling downtown.

Bright, Southold Studio Apt near beach & town

Pied a terre on the North Fork, in the heart of Southold village. Gorgeous bay beach 5 minute walk, as are farmstands, supermarket, Historic Southold Village with quaint shops, Hampton Jitney & LIRR. Lots of light, new contemporary space featuring full bathroom with bathtub. Perfect for one, suitable for a couple for weekend getaway. Small kitchenette perfect for simple food prep, morning coffee/tea. Chickens on property, fresh pastured eggs in your kitchenette upon arrival!

Charming Chester Retreat - Cottage

*Summer's Here** Book your Cottage stay minutes from Chester's town beach: This 2 bed, 1 bath unit has been redesigned to feature a modern kitchen, soaking tub and wood-burning fireplace. The unit also includes a roof deck that overlooks our mature maple trees and a sprawling front porch, complete with rockers. Beach Access 10 min away at Cedar Lake. Great for 1-2 couples, small families or group of friends—Ask about our single roll away bed or pack' n' play(s). Kid friendly!

Lovely Garden-Level Apartment in Heart of Town

This garden-level apartment is centrally located within walking distance to Main Street's retail shops, restaurants, and grocery/pharmacy, and just minutes from The Lace Factory and Deep River Landing, Essex Steam Train & Riverboat, Connecticut River Museum, the CT shoreline and beaches, and so much more. A charming historic home over 200 years old with a classic New England feel, the apartment has two bedrooms, one full bath, and an eat-in kitchen complete with amenities.

Private apartment in the heart of Old Lyme village

This rare village gem is located in the heart of historic Old Lyme, CT. The freshly renovated two bedroom apartment with private entry is a quick walk to the historic arts community, a block from the river for exploring and a quick ride to lake or beach. The property features various flower and vegetable gardens with a stunning pergola and patio for outdoor dining. Conveniently located off I-95 to access nearby quaint New England waterside towns, shops and restaurants.

Large Waterfront Luxury Apartment

Located in Downtown Historic New London, this waterfront apartment features astounding views of the Thames River and Long Island Sound. Conveniently located, the apartment is within walking distance to restaurants, bars, galleries, the Amtrak train station and the Ferry terminals which service Block Island, Fishers Island and Long Island. The apartment also boasts a large deck overlooking the Thames with access to a grill and sitting area.

Penny Corner Airbnb

My place is located up the hill from Good Speed Opera House. The Opera House is on the same side of the river as my place. The folklore is that vacationers used to pay a penny to have their belongings transported by ox and wagon from the port at the river to this corner. A two family home built in 1884. The space is a ground level 1 bedroom apartment with private entrance. There is no TV in the unit, WIFI is available for your devices.

Chester Village 'Pied-à-terre' above art gallery

Our lovely apartment is well designed in an ideal location. A sunshine filled living room w/high ceilings, a private bedroom in back, and large private deck overlooking Pattaconk Brook. A true gem, set up solely for the comfort of our guests. Located in the heart of Chester Village, above our art gallery & boutique. We're neighbor to some of the BEST restaurants, art and shopping in CT! We know you'll enjoy your stay!