Holiday rentals in Upper Millpond

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Top-rated holiday rentals in Upper Millpond

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Top guest favourite
A sun-filled living room features a spacious sectional sofa adorned with decorative pillows. A light wood ceiling and large windows contribute to a bright atmosphere. A coffee table with decorative elements sits in the center, and a green door leads to the outdoor space.
Home in Harwich
4.98 out of 5 average rating, 113 reviews

Spacious cottage beach Wychmere < 4 min Central AC

Entire spacious newly renovated modern cottage in Harwich Port. Sun filled open concept living room with a large kitchen island. Great for families ! Less than 4 min drive to Red River beach and Bank street Beach. 3 min drive to Wychmere Beach Club wedding venue. Close to Harwich Port downtown. Centrally located, close to Chatham, Brewster and Dennis. Freedom Cruise Line ferry to Nantucket at the end of our street. Enjoy a hike to Harwich Thompson's field Conservation area. Close to bike trail

Guest favourite
Home in Brewster
4.87 out of 5 average rating, 229 reviews

Water Front Pond House - 3 acre Cape Cod Sanctuary

Extraordinary pondfront sanctuary on Cape Cod. 1300 sq.ft. home sleeps 8 in 3 bedrooms and 1 bath. Private dock and beach area. House is on the Pond and sited on 3 pristine acres - this property offers exceptional privacy with full water recreation opportunities while also being close to everything "Cape Cod". Centrally located in laid-back Brewster, 5 minutes to Bayside beaches, 10 mins to Chatham, Harwich Port, and Orleans. Local owners have 22 years of online vacation rental experience.

Top guest favourite
Two kayaks are stored beside a shed in a natural setting, surrounded by tall grass. A view of the calm water reflects the greenery of the area, while a cozy indoor space showcases a gas fireplace and comfortable furnishings.
Cottage in Dennis
4.96 out of 5 average rating, 143 reviews

Local Beach+ Fireplace + Hot Tub Under the *Stars*

Welcome to the Bayside Retreat! Enjoy the real Cape Cod in this Quintessential Beach Rental Featuring: Private hot tub, outdoor patio & sofa set in a peaceful backyard 🕊️ 2️⃣ Kayaks- Outdoor Shower- Gas Grill 🔥 Indoor Gas Fireplace ❄️ Mini Splits ✔️Games ✔️Washer/Dryer 📺 55” Sony TV w/ Apps & DirectTV 🛋️ Comfy Furnishings➕Stocked Kitchen Watch the birds, relax out back in peace & privacy or go explore! 📍 Centrally located ❌ NO FEES ⛱️ Year Round Beach Vacation ➡️Bayside_Retreat_Capecod

Top guest favourite
Cottage in Dennis
4.98 out of 5 average rating, 215 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 favourite
A patio area is presented with four modern seating chairs around a central table. The shaded space features a view of the lake, with grassy grounds extending to the water. Two kayaks are visible in the background, indicating recreational options nearby.
Home in South Yarmouth
4.95 out of 5 average rating, 258 reviews

Waterfront Spa|Hot Tub+Cold Plunge in Lake|King bd

✅All linens provided & beds made ✅ King bed / Queen / Twin over Full bunk ✅ Direct lake access = natural cold plunge Follow with hot tub recovery! ✅Waterfront hot tub for 6 -Open year round ✅Fully kitchen w/Carrera marble counters ✅Large waterfront dining rm ✅Gas Fireplace in living rm ✅Level backyard to lake ✅Dock for swimming & fishing ✅2 kayaks & 2 SUPs / beach chairs ✅Deck w/sitting & dining area ✅Patio w/seating & gas fire pit ✅Pet fee $30/day ✅W/D Locally managed

Top guest favourite
A charming two-story home is nestled among the trees, featuring a gray exterior and a welcoming red front door. Lush green shrubbery and blooming flowers are visible near the entrance, enhancing the natural setting.
Home in Brewster
4.92 out of 5 average rating, 152 reviews

4BR/3B | Pond | BikePth | W/D | FireTbl | AC |Deck

Updated, spacious, peaceful Mid-Cape home Private road, private beach/pond (5 min walk) Silent central AC 4 BR/3 full bth: > Ground floor: 2 BR + 2 bth - sleeps 4 > Upstairs: 2 BR + 1 bth - sleeps 4 Hardwood Floors Large, screened porch Large living room: 2 recliners, leather couch, Jøtul gas stove, Roku TV Wooded yard - gas fire table, grill Ping Pong - (in unfinished basement) Near 25-mile long Bike Trail, beaches, golf/mini-golf, tennis, boating Please, no smoking

Top guest favourite
The cottage is surrounded by lush greenery and landscaped yard, featuring a private deck with outdoor seating and a table. A tall evergreen and flowering plants enhance the serene environment, while large windows reflect natural light from the sky above.
Guest house in Brewster
4.92 out of 5 average rating, 270 reviews

Charming Antique Cape Cod Cottage

Our cottage is situated in a lovely, landscaped yard with a private deck and back yard for our guests. We have a self check in that allows for privacy. While there is a feeling of privacy, you are close to stores and other conveniences. There are many walking trails nearby and beaches for outdoor activities. Perfect location for getting away or seeking adventure. Be sure to check out our fall and holiday specials. OCTOBER, NOVEMBER AND DECEMBER - BOOK 3 NIGHTS GET FOURTH NIGHT FREE!

Top guest favourite
A bright living area features a spacious gray couch alongside a round wicker coffee table. Large windows allow natural light to fill the room, and a dining table with six chairs is positioned nearby. The light wood flooring enhances the open atmosphere.
Cottage in Harwichport
4.95 out of 5 average rating, 399 reviews

Newly renovated Cape Coddage! Location! Location!

Newly renovated! Harwichport home- 2 min walk to beach, sleeps 10. Located right by Bank St Beach In Harwichport! Walk 1-2 minutes to the beach or walk 1-2 minutes in the other direction to Main Street where you will find shops and restaurants. Ember, The Port, 3 Monkeys, Beer Garden, and Mad Minnow. This home is in the dream location. Pull in and you don't need to drive until you leave. Walkable to Wychmere beach club. This home is often shared by guests of events celebrated at Wychmere.

Top guest favourite
The exterior of a charming cottage is visible, featuring natural cedar shingles and a welcoming porch. Lush flower beds, including vibrant blue hydrangeas, frame the entrance, while a white picket fence adds to the quaint appeal. A well-maintained lawn enhances the home's inviting presence.
Home in Brewster
4.92 out of 5 average rating, 106 reviews

Antique Cape Home With Modern Conveniences

The Elisha Howland Saltbox provides your opportunity to experience the unmatched essence of a true 'Olde Cape Cod' home. We offer a restored antique Saltbox with 2 bedrooms and 2 bathrooms. For an additional charge, there is a detached cottage which can accommodate two more guests. PLEASE NOTE: we accept ONLY FULL WEEK RENTALS from mid-June to mid-September, but we welcome shorter or much longer stays during the rest of the year. Our home is a lovely place to spend a winter on Cape Cod.

Top guest favourite
Guest suite in Harwich
4.99 out of 5 average rating, 635 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 favourite
Guest house in Brewster
4.95 out of 5 average rating, 131 reviews

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.

Guest favourite
A spacious bedroom features a four-poster bed with a light bedding set, complemented by two large, round ottomans. A patterned wall adds texture, while a cozy seating area is visible in the background. Soft lighting enhances the calm ambiance.
Flat in Dennis
4.95 out of 5 average rating, 138 reviews

Apartment suite|Firepit|Private Deck|Pond Access

Enjoy a stylish experience at this centrally-located spot. Our newly built apartment suite is within walking distance of Dennis Port for restaurants, yoga, and an organic market. Private parking, entrance, and deck along w/ water access to Swan Pond. A full kitchen & Bath equipped with a new LG washer + dryer makes this space feel like your home away from home. Explore, play, rest & relax. We have all you need for a wonderful retreat to make your trip to the Cape an enjoyable one.

Popular amenities for Upper Millpond holiday rentals