Vacation rentals in First Encounter Beach

Charming Old Cape Cod

Indulge in relaxation and leisure at Snowtop on the Town Cove. The charming retreat features a private entrance, a spacious bedroom with a king size bed, a full bath, and a sunlit living room with a dining table overlooking picturesque Town Cove. The view in the photo is your front yard. Guests often enjoy sitting outside to watch boats drift by and the sky change color to a sunset. Nestled on a quiet road, Snowtop is 3 miles from beautiful Nauset Beach and 2 miles from the center of Orleans.

New modern style Cape Cod escape

Beautifully furnished,fully renovated 3BD,2BT duplex in a Fantastic location. Spacious yard. At the end of a cul-de-sac. Within minutes of Beaches, Trails, Great Pond and Wiley Park. The open living space invites gatherings of family and friends. Modern bathrooms, fully equipped kitchen with new appliances. Great outdoor space, patio, big tables,grill, plenty of parking, A/C window units, W/D. Sleeps up to 6 people.Linens, towels, beach towels/chairs & an umbrella provided.Peaceful Cape Cod home

Steps to Rock Harbor | AC, Deck, Outdoor Shower

Welcome to Rock Harbor! Just steps from one of Orleans’ most loved harbor areas, this newly renovated Cape Cod cottage blends classic coastal charm with modern comfort. Whether you're heading to the beach, catching a sunset at Rock Harbor, exploring the National Seashore, or day-trip to Provincetown, Chatham, or Hyannis, this is an easy & relaxing place to come home to. Perfect for families, couples, or friends, the cottage sleeps up to 6 & has been thoughtfully designed for a comfortable stay.

5 Min Walk to Bay Beach! Large, Newly Renovated!

A quiet 5-min WALK to Cole Road beach, a 1/2 mile to the Cape Cod Rail Trail and Wiley Pond. Short 7 min. drive to Coast Guard Beach, and 30 min. to Provincetown. Enjoy a quiet, bayside beach vacation in this spacious home, newly renovated! Location is perfect for vacationers looking to relax at the beach and/or be adventurous. Enjoy stunning sunsets every night and relax in this comfortable and roomy home that is peacefully quiet and has everything you need. Sat. to Sat bookings ONLY please!

10 min walk to Beach - Amazing View & Huge Deck

Enjoy an incredible view of Duck Meadow Tidal Marsh from this cozy cottage. Only a 10 minute walk to Boat Meadow Landing, a great bayside beach. Sip your morning coffee on our huge deck while enjoying the view. The deck includes a retractable roof if you would prefer to sit in the shade. Only minutes from incredible restaurants & shops in Orleans. This home includes AC, office space w/ monitors & a natural gas fireplace. Near the Cape Cod Rail Trail, hiking trails and numerous beach options!

Mazi's-A Waterfront/2 Bd/ Dog Friendly Oasis for 4

Heart of Cape Cod proudly presents Mazi’s Cottage, a quaint beachfront escape set directly on iconic First Encounter Beach in Eastham. This updated 1950s coastal gem offers sweeping bay views, unforgettable sunsets, private beach access just steps away, and boutique waterfront living at its finest. With a stunning wall of windows, cozy charm, fire pit, stargazing space, and room for one well behaved dog, Mazi’s Cottage blends classic Cape Cod magic with modern comfort. Fri-Fri in July & Aug

Cape Cod Heaven

Private one bedroom with full bath and balcony overlooking garden and a peek at the bay. Great location less than a mile from beautiful First Encounter Beach, a wonderful bay beach, and five minute walk to freshwater pond with sandy beach. Ocean beaches and bike trail close by. Bring your bikes or kayaks, or rent them, and enjoy all the Cape has to offer. Great for singles, couples, small families. Has a small refrigerator, microwave and Keurig. There is not a kitchen.

Hillside Cottage

A one-bedroom cottage that sleeps 4, nestled into the hillside at the top of the wetland. Great for birding! Located on a beautifully landscaped property walking distance to Lecount Hollow Beach. The bedroom has a queen bed and there is a queen and a single sleep sofa in the finished basement. There is also a studio apartment available on the premises that sleeps two. The listing name is "Comfortable Studio Apartment".(Pets are allowed in the studio appartment)

National Seashore Escape

There is no interaction required with hosts during stay. 1/4 mile to National Seashore Salt Pond Visitor Center and 2.0 miles to Coast Guard Beach, rated America's 6th best beach in 2019 by Dr Beach. The studio is above the garage with a private entrance private bath with shower. Queen bed, wifi, whisper quiet mini split a/c no window unit, tv. There is a kitchenette with refrigerator, microwave, coffee maker, toaster, sink, no stove.

Beachfront Cottage on White Pond (Marshmallow)

Our Cottage sits directly on White Pond tucked away on acres of private property. Our cottage offers a private beach, deck, outdoor shower, outdoor dining area all while enjoying Cape Cod. White Pond is ideal for swimming, boating and fishing. The bike path and well known beaches are less than 2 miles and near to many delicious restaurants. There is another cottage on this property that sleeps four if you have other guest wanting to join

Beautiful home & backyard oasis

Lovely, large 4 bedroom home on a quiet cul-de-sac in South Eastham. Walk to Herring Pond, minutes to either Boat Meadow or First Encounter Beaches, close to Bike Path and very convenient to National Seashore Park. Beautifully landscaped backyard with outdoor kitchen, and fire pit lounge area and screened in porch. This is a perfect house for a large family or for more than one family.

Cottage at Turtle Crossing

A nature lover’s paradise- sit and watch the tide and enjoy one of Eastham’s beautiful tidal marshes and beach. 5 min walk to first encounter beach or a short drive to some of the Cape’s best beaches. This cozy cottage will make you feel right at home. Enjoy one of the Cape’s most sought after sunsets from the deck or even the couch through our picture window!