Apartment vacation rentals in Chatham

Ensign Suite (Apartment E) 63 Pleasant St. Hyannis

This is a fully-furnished Apartment (En-Suite) located at 63 Pleasant Street. This apartment features a living room area (with 4k OLED TV), bedroom w/ extra long queen bed, a pull out murphy bed, and a pull out couch bed. Kitchen: coffee maker, stove, dishwasher, etc. Single bathroom. This unit is found in a neighborhood called 'Ship Captains Row" which is located in walking distance from both Main St, Hyannis as well as Hyannis Harbor. We also have on site parking for at least 2 cars.

Beautiful Creekside Apartment in Wellfleet Center

Unique romantic apartment overlooking Duck Creek. One large living space which includes kitchen, work area, dining and air conditioned living room with a spectacular view. Queen bedroom and full bath. Small outdoor sitting area with table and chairs to watch the tide role in and out. See the sky change color at sunset and if lucky, catch the moon rise. Access to this private apartment is up a spiral staircase. Close to all of Wellfleet's restaurants, art galleries, town center and the pier.

Songbird Studio- Secluded but close to everything!

Bright, sunny, secluded, green 600 sqft studio apartment at rear of Antique home in the heart of Brewster, Northside of Rt 6A. Private entrance. Private backyard with lawn & gardens. Small private deck, gas grill. Bird and small animal life abounds outside. Tons of stars at night.. salt air on the wind. Walking distance to coffee shop, convenience store, multiple restaurants, Bike Trail. Short car ride to bay beaches, easy drive to Ocean beaches. Gas "woodstove" for heat, AC for cooling.

The Knoll

A quiet home nestled next to conservation land at the end of a dirt road. Though there are neighbors, the landscaping creates a private oasis. The downstairs apartment with private entrance is old New England with Cape Cod affects. The Bedroom has a queen bed. Second sleeping area has a Daybed with trundle and is partially open to the living area. Outside deck has a grill and shower for guest use. Close to School House pond, bike path, and 3 miles from beaches, shopping, and downtown.

Apartment suite|pond access|Firepit|Private Deck

Enjoy a stylish experience at this centrally-located spot. Our newly built apartment suite is within walking distance of Dennis Port for restaurants, yoga, and an organic market. Private parking, entrance, and deck along w/ water access to Swan Pond. A full kitchen & Bath equipped with a new LG washer + dryer makes this space feel like your home away from home. Explore, play, rest & relax. We have all you need for a wonderful retreat to make your trip to the Cape an enjoyable one.

The Cape Cod Perch at West Dennis Beach Studio Apt

Take it easy at this unique and tranquil getaway just a short walk from three Nantucket Sound beaches. This 300-square-foot studio apartment on the second floor of our home. With a brand new Weber grill, picnic table, and fire pit, there is plenty of outside living. Trotting Park, South Village, and West Dennis Beaches are all walkable. Enjoy food from Sandbar, Swan River Seafood, Chapin's, Cleat & Anchor, & Bandera's Market in the summer. Call off season.

Cute Cottage Near Beach & Main Street 3BR/3BA (15)

Stay at a charming 3-Bedroom cottage in a beautiful setting within walking distance to Cape Cod's warm sandy beaches and Main Street Hyannis. Captain Gosnold Village is ideally located within a short walk from three of the Cape's best beaches and nestled between picturesque Hyannis Port and the vibrant atmosphere of Hyannis Harbor with its island ferries, sightseeing and fishing charters.

Cozy Waterfront Apartment, Private Beach Access

Charming living space with nautical decor invites you to unwind off the grid for a few days. There is a window seat for reading, small high top for morning coffee, and all the accessories for a relaxing day at the beach. A five minute drive into town for local shopping and dining. Many scenic trails for walking and biking. Make us your base as you explore Cape Cod’s beautiful shores!

Walk to private beach, spacious peaceful apartment

2026 RESERVATIONS CALENDAR WILL OPEN SEPT 1. Fully separate, pristine 1-BR apartment a short walk from Little Pleasant Bay, in our secluded home on wooded lane, looking out on a small pond. Private entrance and stairs to airy, light-filled, tastefully furnished rooms, with full kitchen and private laundry room. Near Orleans and Chatham.