Vacation rentals in Upper Millpond

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Top-rated vacation rentals in Upper Millpond

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favorite
A bright kitchen area features a fully equipped setup with a washer/dryer combo and a cozy dining nook for two. A peaceful view of the water is displayed alongside a comfortable outdoor seating arrangement around a fire pit. A nicely decorated sleeping area includes a spacious bed with soft linens.
Tiny home in Brewster
5 out of 5 average rating, 74 reviews

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

Top guest favorite
An outdoor seating area is presented with plush, striped furniture and a large firepit at the center. A bright turquoise umbrella provides shade, while the tranquil waterfront view showcases shimmering water and greenery. Potted flowers add a touch of color to the serene setting.
Home in Harwich
4.96 out of 5 average rating, 84 reviews

Waterfront★ Pvt Beach ★ On Bike Path ★Bikes★Kayaks

*Beautifully decorated waterfront cottage w/ bluestone patio- private beach 🏡 * Directly on Cape Cod Rail Trail Bike Path 🚲 *Sunsets from the couch 🌅 *Central A/C ❄️ *Private sandy beach on crystal clear lake 🏖️ *2 Kayaks, 6 Bikes & 2 SUP’s incl- 🛶 🚲 saving $400-$600 in rental fees *6min drive to Bay Beach🏝️ *Large waterfront LR w/65" Frame TV 📺 * Beds-1 king, 1 queen, 2 twins 🛌 *Gas Fire-table 🔥 *Outdoor shower 🚿 *Woodburning FPL in LR * Pet friendly-$30/nt 🐶 😺

Top guest favorite
Home in Harwich
5 out of 5 average rating, 25 reviews

August Avail! 2 Mi. to Beach+Rail Trail+Wychmere

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

Top guest favorite
Home in Eastham
5 out of 5 average rating, 9 reviews

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!

Top guest favorite
A wooden sign is displayed, featuring a welcoming message that reads 'welcome to Cape Cod.' The text is artistically styled, with blue waves and a small sailing boat illustrated underneath.
Guest suite in Brewster
4.97 out of 5 average rating, 409 reviews

Sheep Pond Get-Away

The AirbNB Studio Space is Private w/ its own separate entrance & exit. Our home is set in the 'Sheep Pond' area. We are walking distance to Sheep Pond to kayak & swim. We have kayaks, paddleboards, beachchairs, & towels for your use. A backyard w/ your own picnic table, seating area, & hammock. An outdoor shower ! Minutes away from bay & oceanside beaches, biking, hiking & Nickerson State Park. 40 mins from Provincetown; & surrounded by quaint Route 6a, restaurants & shopping !

Top guest favorite
A spacious backyard features a well-maintained lawn, surrounded by lush greenery. A wooden deck with seating overlooks the area, complemented by colorful flower pots. A hammock is nestled between trees, inviting relaxation. Comfortable chairs are arranged for outdoor enjoyment.
Guest suite in Harwich
4.99 out of 5 average rating, 656 reviews

Romantic getaway suite

GENEROUS DISCOUNT FOR LONG TERM OFF SEASON STAYS. ( February, March, November, and December) Contact direct. Ten 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.

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 Port
5 out of 5 average rating, 9 reviews

NEW 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

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

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, 327 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, 593 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

Popular amenities for Upper Millpond vacation rentals