Holiday rentals in Upper Millpond

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Top-rated holiday rentals in Upper Millpond

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

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Top guest favourite

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 South Dennis

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 *Driveway abuts road, cars can be heard* 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

4.96 out of 5 average rating, 73 reviews

Top guest favourite

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.

Guest house in Brewster

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.

4.97 out of 5 average rating, 30 reviews

Top guest favourite

A charming single-story home is presented with light grey shingles and dark blue shutters. A paved pathway leads to the front door, framed by manicured green lawns and landscaped flower beds. Trees and shrubs add to the serene outdoor environment.

Cottage in Harwich Port

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.

4.95 out of 5 average rating, 432 reviews

Top guest favourite

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

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.

4.99 out of 5 average rating, 670 reviews

Top guest favourite

A spacious, modern kitchen area features a large island with a dark base and white countertops, accented by pendant lights above. To the side, an open concept living space includes a comfortable seating arrangement and dining area, with natural light streaming in through large windows.

Home in Harwich

Spacious cottage beach Wychmere < 4 min Central AC

Entire spacious newly renovated modern cottage in Harwich Port. Open concept living room with a large kitchen island. Great space for families ! Bank street Beach and Wychmere Beach Club wedding venue are 4 min drive from us ! We’re very close to Harwich Port downtown with great restaurants. We’re centrally located, close to Chatham, Brewster and Dennis. Freedom Cruise Line ferry to Nantucket at the end of our street. Enjoy the bike trail nearby with rental location if needed.

4.99 out of 5 average rating, 137 reviews

Top guest favourite

A bright living area features large windows overlooking a scenic marshland and ocean view. A cozy cream-colored couch and an armchair are positioned near a glass coffee table, inviting relaxation. Natural light fills the space, enhancing the tranquil ambiance.

Home in Chatham

The Osprey Nest - Beach house with stunning views

The Osprey Nest is a classic Cape Cod beach house just steps to the ocean with panoramic views across the protected marsh. A cozy and timeless retreat, with modern amenities and spacious and light-filled rooms. This home has been in my family since the 1960’s and you will feel the warmth and charm the minute you step in the door. The location is perfect for nature lovers but within 10 minutes of stores, restaurants, and charming towns. A perfect base for Cape Cod sightseeing.

4.97 out of 5 average rating, 178 reviews

Top guest favourite

Home in Yarmouth Port

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

4.99 out of 5 average rating, 133 reviews

Guest favourite

Home in South Dennis

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.

4.86 out of 5 average rating, 7 reviews

Top guest favourite

A game area features a colorful 'Roll and Score' arcade game highlighted by vibrant blue lighting. The background displays a large Boston Red Sox-themed mural, enhancing the playful atmosphere. Beside the arcade game, a shuffleboard table contributes to the entertainment options available.

Home in Harwich

* Game Room, Linens, Quiet St, Central AC/Heat

Cape Cod - Harwich/Dennis Line - Entire Home, 6 Beds + Futon (4 Bd/2 Ba), Includes 2 King Beds, Seasonal Outdoor Shower, Linens Included! Central A/C, Game Room, Cable, Wifi, Pet-Friendly, Near Beaches, Golf, Shopping & Attractions. Great Central Location at CapeVaca. Nearby Beaches: Mayflower, Earle, Pleasant Road, Corporation, West Dennis, Crowe's Pasture, Paines Creek, Harwich, Dennis, Brewster. Message us for early check-in options during the off-seasons.

4.98 out of 5 average rating, 178 reviews

Guest favourite

A cozy sleeping area showcases a patterned bedspread with floral designs, complemented by matching pillows and a neatly arranged stack of towels. A bedside table holds a lamp and a small bouquet, while a striking floral wallpaper adds warmth to the room.

Home in Brewster

Luxury Beach House! Firepit&PetoK&2Kingbeds

⚓️THE CAPTAIN’S HOUSE ⚓️ *sleeps 8 (max 6 adults) * sq ft *2 king beds *1 queen *1 twin *1 tiny twin (38”W x 62”L) *3 full bathrooms *Laundry room *Gas fireplace *4 Smart TV’s/1 frame TV *Fullequipped kitchen *outdoor fire pit/seating (propane) *Dining for 8 *Cotton linens/towels provided *Dedicated Workspaces (2) *High Speed WiFi * Under 5 mins away=Paines Creek Beach, Drummer Boy Park, Cape Museum Natural History, and more! *1 dog allowed $30/per night pet fee

4.96 out of 5 average rating, 84 reviews

Top guest favourite

Home in Brewster

4BR/3B | Walk2Pond | Screened Porch | FireTbl | AC

Relax at this spacious mid-Cape retreat on a quiet private road, just a 5-minute walk to a private swimming beach and pond. Canoe included! Sleeps 8 with 4 bedrooms (2 on the main level, 2 upstairs) and 3 full baths with bidets. Enjoy central A/C, hardwood floors, a screened porch, 65" OLED TV, gas stove, gas fire table and grill, ping pong, and wooded yard. Convenient main-level washer/dryer. Near the Cape Cod Rail Trail, beaches, golf, tennis, boating.

4.93 out of 5 average rating, 165 reviews

Top guest favourite

A sandy beach area is shown, populated with visitors enjoying the sun and water activities. Small boats are visible in the distance, while people are seen wearing casual summer attire. Beach chairs and umbrellas are scattered throughout the shoreline.

Home in Chatham

The Chatham Bars White Foam House Steps From Beach

Settle back in one of the rocking chairs on the front patio and take in the views of the harbor. Charm and warmth abound in this Cape Cod cottage with Chatham Seaside Links located across the street. Leave the car and walk to local restaurants and shops. Watch band concerts at the park and bask in the views from the Chatham Lighthouse. Go for a long stroll along Claflin Landing Beach all the way to the Fish Pier and buy the day's fresh catch.

5.0 out of 5 average rating, 29 reviews