Holiday rentals in First Encounter Beach

The Farmhouse - walk everywhere -2 pkg spots

View the Pilgrim Monument from the upstairs deck, with 2 private decks to choose from. The updated interior serves a modern twist on the traditional farmhouse with a mid-century flair, all showcased under open vaulted ceilings. This townhouse is the right-hand portion of the farmhouse, which has been divided into two townhouses. Lovely open airy vaulted ceilings with plentiful natural light fill the space. Serene yet invigorating. You have TWO private parking spaces to use! The front porch & the two decks in the back are yours exclusively. Shared laundry in basement with one unit. Text us anytime. The Farmhouse is a historic property located on a quiet street right in the center of town. Shop and browse galleries on Commercial Street, and visit the nearby Long Point Light Station. Bike and hike along the Cape Cod Provincelands Trail. We have parking for 2 cars. Many guests park and walk everywhere. Some bring their bikes and or rent them. The town also has pedi-cabs which are fun - and there is also Uber and Lyft. It’s a breeze to get anywhere. Please be advised that the rate you pay/the listed rate, already includes taxes of 5.7% State Tax, 6.0% Local Tax, and 2.75% Cape Cod & Islands Water Pollution Fund Tax

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.

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.

Claw Foot Tub & King Bed at Club Tanuki Cottage

Glorious gardens and bay breezes! King-sized Casper bed in romantic antique Cape Cod studio cottage with private entrance & patio, in-room double-slipper claw foot tub, luxe bath amenities, Brooklinen sheets. Just renovated soup-to-nuts! Marble & antique wooden floors, decorated with rotating collection of antiques, original local art & great light. Nestled along historic route 6A (Main Street) near other galleries, museums, walking trails, ponds and beaches; 90 seconds to closest beach.

Journey’s End Beachfront Cottage with Parking

Escape to the beach and enjoy the Journey's End! This gem of a revived fisherman's cottage is nestled on the beach & provides 180-degree views of unspoiled White Horse Beach on the Atlantic Ocean with uninterrupted views of sea, sky, sunrises, & sunsets. It is THE spot to relax, walk the beach, watch the ships, stargaze, or enjoy a meal oceanside. With its private beachfront deck & beach stairs & one off-street parking space (a rarity), the Journey’s End lives up to its name for vacationers!

Cape Cod Farmhouse: Walk to the Beach in Brewster!

Defined by understated furnishings throughout, The Brewster Farmhouse is a serene beach retreat, right across the street from Ocean Edge Resort and a 10 minute walk to Ellis Landing Beach. Total of 3 bedrooms and 4 full bathrooms, with central AC and heating. All bedrooms have queen-sized beds, and their own private, en-suite bathrooms. Right next door to cute antique shops, art galleries, and boutique farms. Close walk or drive to all of the best restaurants and cafes in Brewster!

Vintage 1940s Cottage 6 mins to beaches and trails

Wake up surrounded by peaceful pines at Blueberry Cottage, a 1940’s Cape Cod tiny house minutes from Coast Guard Beach (ranked the #1 beach in New England by Travel&Leisure Magazine), freshwater ponds, and the Cape Cod Bike Trail. Launch a kayak or paddleboard at nearby Hemenway Landing with stunning salt marsh views. Enjoy a fully equipped, updated kitchen, mini split air conditioning/heat, ceiling fans, and a new hybrid queen mattress. The cottage offers WiFi and a smart TV.

4 Season Cottage, Nauset Beach, tennis court

A four-season, luxurious, cottage-style retreat near the glorious beaches on the North spit of Nauset Beach, off Nauset Heights. Tennis court, ample grounds, walking neighborhood, and easy beach access. This Property is shared with two seasonal cottages. Perfect for getaways, the cottage is designed for a couple or individual. While there are two twins downstairs, these are appropriate for children, a friend, or a relative who will not be jealous of the king room upstairs.

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.

Waterfront Modern Home in Eastham, on a Pond

Escape to this peaceful 2BR home in Eastham, where your backyard leads right to a serene pond—perfect for morning coffee, paddleboating, or simply relaxing by the water. Located near beaches, trails, and local spots, this cozy getaway offers comfort and nature all in one. Enjoy a fully equipped kitchen, spacious living area, and beautiful views right outside your door. Ideal for couples, families, or friends seeking a Cape Cod retreat. 19F - Hosted by Tuxfin Hospitality

Steps to the Sand with Amazing Seaside Views

Escape to this rare beachfront retreat where the ocean is your front yard. Unlike inland rentals, this studio condo offers direct beach access and the calming sound of waves to lull you to sleep. No driving, no packing—just step outside and you're there. Enjoy coffee on the deck, spend the day swimming or sunbathing just steps away, and watch the sunset over the water—all without leaving home. It’s the kind of coastal escape inland properties simply can’t match.

The Sea Captain's Carriage House

The 1840s Carriage House has been beautifully remodeled. The first floor has a living room, dining area, kitchen, and powder room with washer/dryer. The backyard deck has seating for four and a Weber gas grill. Upstairs, the large, elegant bedroom features a king-sized bed, sitting area, reading nook/twin bed, writing desk, and ensuite bathroom with shower. The half acre property offers beautiful gardens for you to enjoy and a delicious outdoor shower.