Vacation rentals in Upper Millpond

BlueSky Cottage! Tiny Luxury! Firepit/patio/petOK

Blue Sky Cottage 💙 ⛅️ -located within The Salty Doors Cottage Community! 🌟Fully renovated 🌟 Fully equipped kitchen 🌟 Washer/Dryer combo 🌟High quality memory foam Queen mattress 🌟 Cotton linens 🌟 Down pillows/blankets 🌟 Cotton towels 🌟 Shower toiletries 🌟 Custom dining nook for 2 🌟Private screened in porch 🌟Private patio-propane fire pit 🌟 BBQ propane grill 🌟 Two 43” smart TVs 🌟 Stand up shower/full BR 🌟 1 pet allowed 30lbs and under *additonal $30/per night pet fee will be due after booking

Sept. Avail! 2 Mi. to Beach/Wychmere+3 King Beds

This beautiful home sits on a large shaded lot and is positioned along the Cape Cod Rail Trail, which runs behind the home. Large fully fenced-in yard with a lovely shaded patio area. • 2 miles from Wychmere Beach Club • 3 Kings, 2 Twins, Clawfoot Tub • Outdoor Shower, Beach Chairs & Towels • King Pine Floors Throughout • Banquet Dining Area that Seats 8 People • Fire Pit and Adirondack Chairs • 10 minutes to Dennis & Brewster • 15 minutes to Chatham & Orleans • 4-5 Car Parking in the Driveway

Sunset on Shore - Lewis Bay Waterfront

NEW LISTING! Built in the 1930s, this is the kind of beach house that invites you to unplug (don’t worry-there’s WiFi). With views of Lewis Bay from every room, private stairs to the water, a big deck, lawn, and outdoor shower, it’s all about the location and the view. Inside, it’s Olde Cape Cod-window A/C, a butter-yellow kitchen, and the kind of charm that takes you back-nostalgic in all the right ways and the best seat for every sunset. Bring your boat-a ramp is located at Englewood Beach.

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.

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!

Billy's Beach Bungalow

Step into vacation mode at this stunning, fully remodeled Cape Cod retreat, designed to deliver the ultimate coastal getaway. Located on the exclusive bay side of South Dennis, you’ll be less than 10 minutes away from Mayflower Beach, Corporation Beach, Chapin’s Bayside and more! Enjoy high-end finishes, a designer kitchen, two spa-style bathrooms, and a finished basement perfect for entertaining. Outside, relax in a private fenced-in yard with an updated outdoor shower, deck, and fire pit!

Romantic getaway suite

GENEROUS DISCOUNT FOR LONG TERM OFF SEASON STAYS. ( February, March, November, and December) Contact direct. Eleven year old private one bedroom lavish suite over two car attached garage with private entrance, deck, and parking in a quiet neighborhood central to all the Cape has to offer. Beautifully furnished with central air, gas fireplace, hardwood floors, double slipper clawfoot soaking tub, separate subway tiled shower, wireless internet and Sony 49 inch 4KUHD edge -lit streaming TV.

Nehemiahs Nest: Healing Cape Cod Pond View Cottage

18+ Lovely waterfront tranquil getaway. All nearby houses hidden! This gem of a spot has been curated to soothe the soul! The cottage is sitting on Bakers Pond with an unobstructed view surrounded by conservation land *The driveway abuts a road* Wildlife can be observed. Swim or fish in this very clean kettle pond! The edges of the pond require water shoes for comfort as this is a natural body of water with no man-made beach/interference of nature. Kayaks, and life jackets available

*Newly Renovated | Private Yard & Deck

Enjoy the ultimate Bay Side getaway in this charming Dennis ranch! Located near world-class North Side beaches like Cold Storage and Mayflower, this updated 2BR home features a modern granite kitchen, sun-drenched living spaces, and hardwood floors. Relax on the sprawling wrap-around deck or the private patio overlooking a quiet wooded yard. After a day at the shore, rinse off in the quintessential Cape Cod outdoor shower. A peaceful, single-level retreat for your coastal escape!

Luxury Waterfront - Hot Tub, Deck & Waterviews

Welcome to Aunt Laura’s Retreat, a newly renovated waterfront home ideal for families and groups seeking a relaxing Cape Cod getaway. Enjoy beautiful water views from every room, direct access to Swan Pond for kayaking and beautiful sunsets to end the day. Unwind in the hot tub, dine on the deck overlooking the water, or relax on the lower patio with a grill and cozy seating. - Direct access to Swan Pond - 5 min drive to Sea Street Beach - Close to Cape Cod Rail Trail & dining

Cape Cod Cottage by the Bay!

Classic, beautifully crafted, newer cottage by Cape Cod Bay. All amenities. Stainless steel kitchen, Cathedral ceilings, Wide plank wood floors, water view. 2 min walk to one of the best beaches on the Cape! Quiet locale in the historic village of Quivet Neck, within East Dennis. 35 miles to Provincetown. I do not allow pets. I have family members with severe allergies who use the cottage. There is no AC at this cottage. I have 15 windows, 4 fans and an ocean breeze.

Dog-Friendly Home w Pond Access and Canoe, for 7

Wake up near the water, walk 3 minutes to the neighborhood pond for swimming or taking out our canoe or paddleboat for a row. Later, unwind on your quiet backyard deck or by the fire pit after a beach day. This dog-friendly Cape home is designed for easy family getaways—with a king 1st floor bedroom, 5 beds total, open living space, and room to relax inside and out. The home has hardwood floors, cathedral ceilings, and is minutes to Cape Cod Bay and Nantucket Sound beaches.