Holiday rentals with a patio in Eastham

Cape Cod cottage with 3 bedrooms near ocean & bay!

Bring your family to this newly updated cottage in Cape Cod. The house has 3 bedrooms, including a kids bunk room. Bay beaches are 1.2 miles away & ocean side beaches are nearby! Close access to the Cape Cod Rail Trail (0.5 miles away). When you’re not at the beach, enjoy cooking on the BBQ grill, playing games/puzzles, using the kids’ art table, having a campfire, or lounging in the family room. Cooler, chairs, & sand toys are available. Enjoy the outdoor shower too. Fun memories to be made!

Bayside Eastham Apartment

Retreat to this private 1 BR/1 BA apartment 1 mile from Cape Cod Bay in a quaint, quiet neighborhood. Features include updated full kitchen, complimentary coffee/espresso bar & cooking essentials, fully dressed queen bed and bathroom necessities included. All you need for the beach is provided - 5 minutes from Cape Cod National Seashore Beaches, fresh water ponds, Cape Cod rail trail, Wellfleet Drive-In and a 25 min drive to Provincetown. Pack light, kick back and relax on the sun kissed deck!

Lovely House 5 Min to Beach - Deck, Grill, Garage

Just 5 minutes from Cape Cod's stunning beaches like Rock Harbor and near Orleans' many shops & restaurants. This spacious home has a bright sunroom, AC, deck + grill, garage to park in, beach chairs & toys, dedicated workspace, and a fully equipped kitchen. Games & puzzles available for rainy days. Bike along the Cape Cod Rail Trail, with an entrance near our home, or go Hiking at a nearby trail. Ideal for families or groups, this home offers the perfect balance of relaxation and adventure.

Huge Roof Deck Overlooking Ocean. Paradise Awaits!

300ft to amazing Kingsbury beach Oceanview from your bed, dining & family room Huge roof deck overlooking ocean. Amazing sunsets! Game room w/air hockey, Foosball, ping-pong, family board games, etc 2 large couch areas w/75” TVs so adults & kids have separate hang out spaces Large upscale kitchen Outdoor shower 5min bike ride to Cape Rail Trail Laundry, AC/heat for year-round use All linens, bath & beach towels provided 2 large side yards where kids can play Beach chairs, beach toys, etc

Sweetbriar ~ Charming Cape Cottage ~ Dog-Friendly!

Discover Sweetbriar, a 1940s two-bedroom 600 sqft Cape Cod retreat in Eastham’s peaceful Cottage Grove. Minutes from First Encounter Beach and Fort Hill, this cozy, dog-friendly cottage blends classic charm with modern comfort. Relax on the private deck, explore scenic bike trails, and unwind in a warm, inviting space. With easy access to beaches, villages, and nature, Sweetbriar offers the perfect escape for unforgettable Cape Cod days. Book now and experience the magic of the Cape!

Brand new, on a secret pond

Welcome to our chic guest house. This brand-new retreat includes a bedroom with king bed, a living room with a sofa bed, smart TV, sleek breakfast bar, and a contemporary bathroom with rainshower and a heated towel rail. Steps away the beach invites you to relax by the water of a semi-private pond next to the rail trail. Welcome to a retreat that strikes the perfect balance between contemporary luxury and the tranquility of nature – for those who appreciate the finer things in life.

1850 Orleans Antique Home with Path to Arey’s Pond

Make memories at this private family and pet-friendly 3 BR Orleans antique Cape Cod home with access to Arey’s Pond. Kayak and paddle-board directly to Little Pleasant Bay and beyond. The property was once home to the town tavern on Old County Road en route to Orleans. Enjoy the wrap-around 3 season porch. Antique home with bath and other renovations that were recently completed. We want to share this unique property with those who appreciate the history. Please ask questions!

Sauna · Fireplace · Waterfront · 2 Kings · DogsYes

☆ Waterfront, located on private saltwater beach (with central location) ☆ Sauna (year-round) ☆ Cozy fireplace (electric) ☆ 3-season patio ☆ 1% donated to Cape nonprofits ☆ 2 Kayaks & 2 Paddle boards ☆ Outdoor fire pit & charcoal grill ☆ Ample workspace ☆ Dog Friendly ☆ Washer/dryer ☆ 2 King Beds with 50" TVs in bedrooms ☆ Outdoor shower (open May through fall) ☆ Beach chairs provided ☆ Linens, all towels provided ☆ 10min from bay or ocean beach ☆ 15min MV & Nantucket ferries

Cozy Cape Stay! bike path, beaches, water view!

Set on an idyllic spot between two ponds, our newly renovated cottage has everything you could dream of to create memories year round! INCREDIBLE location for hiking, biking, kayaking and fresh water, bayside or oceanside swimming. Here you will find a New England stay with all the wonders of the Outer Cape but close to Chatham/Orleans/Wellfleet for shopping or dining. A quintessential stay w/ water views, near to ANYTHING you'd want to see and do no matter the season!

Bayside Escape~Short Walk to the Beach (1/2 MILE)

Bayside Escape: Short Walk to the Beach. Newly Renovated. Discover the perfect blend of modern design and coastal charm at Bayside Escape, a newly renovated 3-bedroom, 1-bath home ideally situated on the bayside, just a half-mile from the stunning Campground Beach. This beautifully appointed vacation rental places you at the heart of Cape Cod’s summer fun, with easy access to local attractions, including The Landing for delicious ice cream and more.

Modern Eastham Cottage • Near National Seashore

Located just steps from the entrance to the Cape Cod National Seashore and beside Eastham’s Salt Pond, this modern, light-filled cottage offers a peaceful Cape Cod setting with unbeatable access to nature, bike trails, and iconic beaches — all without the crowds. Coast Guard Beach is accessed by a short drive through the Seashore.

Game Room- Movie Projector Room- Fire Pit

Nestled in the heart of the Cape, our cozy (and beautifully styled) retreat becomes a magical group getaway, why we coined it "Gimlet Getaway". While many envision Cape Cod as a summer playground, it can become the best spring sanctuary for you and your large group! (Pool only open mid-May to mid-Sept)