Vacation rentals in Upper Millpond

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Top-rated vacation rentals in Upper Millpond

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Guest favorite
A compact living area features a muted color palette, highlighted by light green walls. A white sofa is positioned beside a sleek fireplace. The open kitchen is equipped with a washer/dryer combo and neatly arranged dishware. A custom dining nook for two is visible beside large windows, inviting natural light.
Tiny home in Brewster
4.97 out of 5 average rating, 72 reviews

Seagrass Cottage! Tiny Luxury! Patio/firepit/PetOK

Seagrass 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/seating 🌟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

Guest favorite
A modern kitchen is presented, featuring stainless steel appliances and sleek cabinetry. A skylight allows natural light to fill the space. The countertops are finished in a light tone, complemented by a neutral backsplash. A window offers a view of the outdoors.
Home in Harwich
4.93 out of 5 average rating, 28 reviews

7th Vacation in Harwich

Pleasant Lake Region of Harwich with deeded access to Long Pond and Cape Cod Rail Trail bike path. Newly renovated! Bright and Spacious! Sky-lighted modern kitchen, Master bedroom suite. Large deck with benches overlooking the backyard. Central heat & A/C. Hardwood floors. Game room with a foosball. A study area. Washer and dryer included. Outdoor shower. A fire pit and 5 car parking on a driveway on a corner lot make entertaining family and friends welcome! Let your Cape Cod adventure starts!

Guest favorite
Home in Plymouth
4.92 out of 5 average rating, 186 reviews

Panoramic ocean views 100 ft above Cape Cod Bay

Our 5-bdrm Nantucket style beach house has a new kitchen & open living space, with a new deck, all overlooking the entire shoreline of Cape Cod Bay from a commanding perch atop a 100-foot bluff. Whales and seals can be seen from your deck. Located in a private community with its own rocky beach access about 5 min walk from the house where you can hunt for shells & observe the ocean wildlife. This beach is ideal for kayaking. Plymouth also boasts 4 of top 10 rated public golf courses in MA.

Top guest favorite
A bright bedroom features a spacious bed with colorful blankets and decorative pillows. A variety of sun hats are displayed on the wall, providing a cheerful accent. Natural light enters through the window, illuminating the cozy interior.
Cottage in Dennis
4.98 out of 5 average rating, 236 reviews

★Waterview ★Pet Friendly ★Kayaks ★Trails ★

Welcome to SEAGLASS COTTAGE! 🔸 200 MBPS WIFI 🔸 Steps to sandy beach on a crystal clear pond 🔸 Pet friendly 🔸 Linens & towels are included. Beds will be made 🔸 Swim, fish or use our 2 kayaks & 2 SUP’s 🔸 Bluestone private patio w/waterviews+charcoal BBQ 🔸 Outdoor shower 🔸 Sunroom w waterview 🔸 Washer+dryer 🔸 Fully equipped kitchen w/Carrera marble counter 🔸Gas firepit 🔸Ductless A/C & Heat 🔸Small library of books, didn't finish the book? Take it! 🔸Pet fee $25/day

Top guest favorite
A spacious sleeping area is highlighted by a king-sized bed adorned with white linens and accented with yellow pillows. A vintage-style claw-foot tub is positioned nearby against a backdrop of richly textured green tiles. Natural light floods the room through a window, complemented by decorative plants.
Guesthouse in Brewster
4.96 out of 5 average rating, 25 reviews

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.

Top guest favorite
A sunlit living area features large windows that provide views of the surrounding trees and nearby pond. A cozy circular chair invites relaxation, while a small dining table with black chairs offers a spot for meals. Green plants add a natural touch to the decor.
Home in Dennis
4.98 out of 5 average rating, 56 reviews

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

Superhost
Home in Dennis
5 out of 5 average rating, 3 reviews

*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!

Top guest favorite
Home in Dennis
5 out of 5 average rating, 128 reviews

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

Superhost
Home in Dennis
5 out of 5 average rating, 4 reviews

Private Beachfront Home: Sleeps 10.

Rare prime summer weeks have just opened up, offering week-long stays only! Experience the ultimate beachfront getaway at this stunning Cape Cod Bay retreat! This renovated home offers breathtaking views stretching from the bridge to P-town. With 5 spacious bedrooms, 2 modern bathrooms, a cozy living room, a fully equipped kitchen, a den, and an office/game area, it's perfect for families and friends alike. *Bed Linens & towels included. Free parking available for 4 vehicles

Guest favorite
The cottage showcases a classic Cape Cod design, framed by greenery and a gravel pathway. A standalone structure is visible with a sloped roof and a front door lined with dark shutters. Sunlight casts a warm glow on the exterior against a clear blue sky.
Home in Dennis
4.93 out of 5 average rating, 326 reviews

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.

Superhost
An open living area features a comfortable gray sofa facing a round dining table and chairs. A full kitchen is equipped with modern appliances, including a stainless steel refrigerator. Natural light brightens the space through large windows, complemented by light-colored wooden flooring.
Cottage in Dennis
4.86 out of 5 average rating, 592 reviews

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

Guest favorite
A bright living area features vaulted ceilings with skylights, enhancing natural light throughout the space. A comfortable couch and modern armchair are positioned around a rustic coffee table. A dining area with seating and views of the pond can be seen through large glass doors.
Home in Brewster
5 out of 5 average rating, 9 reviews

The Pond House - Brewster

*Brand new for 2026* - hybrid electric + wood fired hot tub! Enjoy the ride to serenity as you find our secluded pond house, nestled in the woods of Brewster Immersed in Cape Cod's natural beauty, the comforts of home combined with ever changing views across the pond leaves the perfect combination of relaxation alongside wildlife filled stimulation Perfect couples getaway or beach trip with friends!

Popular amenities for Upper Millpond vacation rentals