Holiday Homes in Orleans

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Check prices for these dates

In two weeks
12 Sept - 14 Sept
In one month
26 Sept - 28 Sept
In two months
24 Oct - 26 Oct
In three months
21 Nov - 23 Nov

Featured Holiday Homes in Orleans

Our top choices for Orleans holiday homes

2 Bedroom, 2 Bath, 1100 sqft, sun porch, eat in kitchen, Washer/Dryer, Gas Grill
Outdoor dining

2 Bedroom, 2 Bath, 1100 sqft, sun porch, eat in kitchen, Washer/Dryer, Gas Grill

10.0 out of 10, Exceptional, (164)
"Place was adorable perfect for what we needed. Perfect location, centralized for all your needs and wants"
The price is AU$487
includes taxes & fees
1 Sept - 2 Sept
2 Bedroom, 2 Bath, 1100 sqft, sun porch, eat in kitchen, Washer/Dryer, Gas Grill
Chatham! 3BR house, large quiet yard, 5 min to beach, walk to shops, restaurants
Dining

Chatham! 3BR house, large quiet yard, 5 min to beach, walk to shops, restaurants

10.0 out of 10, Exceptional, (94)
"Loved our stay. Property is very clean and in a quiet neighborhood close to town and beaches. Host Bonnie was great. Would definitely rent again."
The price is AU$771
includes taxes & fees
1 Sept - 2 Sept
Chatham! 3BR house, large quiet yard, 5 min to beach, walk to shops, restaurants
Hyannis Hideaway in Cape Cod
Paper towels

Hyannis Hideaway in Cape Cod

10.0 out of 10, Exceptional, (2)
"Awesome private property, close to Main Street and Craigsville beach. My friends and I stay in Hyannis every 4th of July and this home was super accommodating for groups and close to everything. Great stay would recommend. "
The price is AU$1,008
includes taxes & fees
8 Sept - 9 Sept
Hyannis Hideaway in Cape Cod
3-bedroom house in charming Dennis minutes to Corporation Beach. Relax & unwind.
Sun-loungers

3-bedroom house in charming Dennis minutes to Corporation Beach. Relax & unwind.

10.0 out of 10, Exceptional, (2)
"Location is very convenient to lake scargo and corporation beach! House was extremely clean. Well appointed. Had games and beach toys and chairs. Great house for family. "
3-bedroom house in charming Dennis minutes to Corporation Beach. Relax & unwind.
Charming updated bungalow with firepit, fast WiFi, & walkable locale near beach
1 bedroom, iron/ironing board, Internet, bed sheets

Charming updated bungalow with firepit, fast WiFi, & walkable locale near beach

8.0 out of 10, Very good, (40)
"Perfect for one or two people, was great for myself and my dog to stay."
Charming updated bungalow with firepit, fast WiFi, & walkable locale near beach
HARWICH PORT SPECIAL PLACE inquire about long-term
Smart TV, fireplace, printers

HARWICH PORT SPECIAL PLACE inquire about long-term

6.8 out of 10, (24)
"Very convenient location, nice location, plenty of room for our group! And being a dog friendly rental was thrilled with the yard. The outside deck was very nice to sit at, very comfortable "
HARWICH PORT SPECIAL PLACE inquire about long-term
Cape Getaway -walk to restaurants & shops, near bay & ocean beaches & rail trail
Fridge, microwave, oven, stovetop

Cape Getaway -walk to restaurants & shops, near bay & ocean beaches & rail trail

Cape Getaway -walk to restaurants & shops, near bay & ocean beaches & rail trail
Stunning Oceanfront Home With Amazing Views ~ Private Beach - capeoceanvista
Interior

Stunning Oceanfront Home With Amazing Views ~ Private Beach - capeoceanvista

9.6 out of 10, Exceptional, (112)
"This property was as advertised. Right on a private beach, the views here are incredible. Make sure you plan to see a sunrise or sunset! Owner is very easy to work with and responsive. "
The price is AU$2,391
includes taxes & fees
21 Sept - 22 Sept
Stunning Oceanfront Home With Amazing Views ~ Private Beach - capeoceanvista
Brand New 5BR - Pool, Hot Tub, A/C – Walk to Beach, Main St. & Ferry - Sleeps 12
Fridge, microwave, oven, stovetop

Brand New 5BR - Pool, Hot Tub, A/C – Walk to Beach, Main St. & Ferry - Sleeps 12

10.0 out of 10, Exceptional, (2)
"The house was spotless and very well organized. My family and I loved our stay — it’s in a perfect location, close to everything: grocery stores, the beach, restaurants, and more. The owner is very communicative and responds right away to any questions. We would definitely love to come back!"
Brand New 5BR - Pool, Hot Tub, A/C – Walk to Beach, Main St. & Ferry - Sleeps 12
Estate with Private pool, tennis court, and playground!
TV, offices

Estate with Private pool, tennis court, and playground!

10.0 out of 10, Exceptional, (6)
"A gathering of 16 women stayed at Bride of the Sea for a 5-night long weekend to celebrate a 50th birthday, and we had an incredible time. The home was immaculate when we arrived - and spacious enough to comfortably accommodate everyone with large spaces to gather or escape for some quiet time. The beds were extremely comfortable. Parking was ample, easily accommodating three cars in the garage and the remaining cars in the driveway spaces. Many in our group are hobby "chefs", so we enjoyed...
Estate with Private pool, tennis court, and playground!
Winslow Acres heated Pool Escape; Pool open May 15 thru mid-Oct! HotTub all yr!
Outdoor pool, a heated pool

Winslow Acres heated Pool Escape; Pool open May 15 thru mid-Oct! HotTub all yr!

10.0 out of 10, Exceptional, (31)
"our family of 7 adults and one baby had a fantastic stay at this house. It is lovely, provisioned with everything you could want in a vacation house, and the owners are very reachable and responsive. This was a perfect house for a week at the Cape!"
Winslow Acres heated Pool Escape; Pool open May 15 thru mid-Oct! HotTub all yr!
Walk to Beach | Parking for 2 Cars | Close to Town
Beach

Walk to Beach | Parking for 2 Cars | Close to Town

10.0 out of 10, Exceptional, (9)
"We had a good time here. The cottage was small, but comfortable. Would stay here again."
Walk to Beach | Parking for 2 Cars | Close to Town
Coastal Cape Cod 3 bedroom close to the beach, bike path & ponds!
Fridge, microwave, oven, stovetop

Coastal Cape Cod 3 bedroom close to the beach, bike path & ponds!

2.0 star property
10.0 out of 10, Exceptional, (17)
"We’d loved our stay. Great house in a great neighborhood. Would love to stay here again!"
The price is AU$1,290
includes taxes & fees
16 Sept - 17 Sept
Coastal Cape Cod 3 bedroom close to the beach, bike path & ponds!
Newly Updated Home Stone Patio & Fire Pit!
Beach nearby

Newly Updated Home Stone Patio & Fire Pit!

9.2 out of 10, Wonderful, (15)
"Great location for my needs. "
Newly Updated Home Stone Patio & Fire Pit!
New 2025 Saltwater Heated Pool & Hot Tub -Less than 5 Minutes from Nauset Beach!
Terrace/patio

New 2025 Saltwater Heated Pool & Hot Tub -Less than 5 Minutes from Nauset Beach!

10.0 out of 10, Exceptional, (4)
"We had a wonderful time at Tim and Emily’s home! It is well equipped and the pool/hot tub was a plus for the kids. Thank you sharing your home and allowing our family to make fabulous Cape memories!"
New 2025 Saltwater Heated Pool & Hot Tub -Less than 5 Minutes from Nauset Beach!
Bright & open private home, close to beach. Renovated clean and pet friendly!
Interior

Bright & open private home, close to beach. Renovated clean and pet friendly!

9.4 out of 10, Exceptional, (26)
"We had a lovely time staying in the cottage. It’s close to many beaches, a short drive to P-town, and nicely appointed inside."
Bright & open private home, close to beach. Renovated clean and pet friendly!
Ocean Breeze Motel - Standard Double
Beach

Ocean Breeze Motel - Standard Double

9.8 out of 10, Exceptional, (52)
"Amazing, clean and great location with friendly and helpful management. "
The price is AU$301
includes taxes & fees
21 Sept - 22 Sept
Ocean Breeze Motel - Standard Double
Beautiful Waterfront Home with Beach, Dock, Deck, & Great Views! capeoceanvista
Property grounds

Beautiful Waterfront Home with Beach, Dock, Deck, & Great Views! capeoceanvista

9.8 out of 10, Exceptional, (32)
"This is our third year staying for a week in July. We like the ease of getting to both the bay and ocean as well as kayaking right off the beach."
Beautiful Waterfront Home with Beach, Dock, Deck, & Great Views! capeoceanvista
FREE BEACH PASS! NEAR CRAIGVILLE BEACH! 4 bedroom in charming Barnstable w/ AC.
Fridge, microwave, oven, stovetop

FREE BEACH PASS! NEAR CRAIGVILLE BEACH! 4 bedroom in charming Barnstable w/ AC.

10.0 out of 10, Exceptional, (1)
"The house was lovely - photos were accurate. The house is located on a busy street but the backyard was great and it was close to everything we needed/wanted. The upstairs space was perfect for kids. Only negative was that there are no dressers in most of the bedrooms so we had to use our suitcases and no dedicated dining room (but we ate outside most of the time anyway). The property managers were friendly, helpful, and very responsive!"
FREE BEACH PASS! NEAR CRAIGVILLE BEACH! 4 bedroom in charming Barnstable w/ AC.
Luxury 7 BR, 4 BA w/ Unique 60 ft Pool, .4 Miles to Beach
Pool

Luxury 7 BR, 4 BA w/ Unique 60 ft Pool, .4 Miles to Beach

10.0 out of 10, Exceptional, (71)
"Very homey, spacious place!"
Luxury 7 BR, 4 BA w/ Unique 60 ft Pool, .4 Miles to Beach
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Orleans Hotel Reviews

Red Jacket Beach Resort

Red Jacket Beach Resort

10/10 Excellent
"The Resort was right on the beach and the facilities were nice. The staff were friendly and helpful and we had a nice stay."
Roger 3-night trip
Posted 1 day ago
Red Jacket Beach Resort

Find out more about Orleans

Find out more about Orleans

Orleans Holiday Homes information

Number of reviews
642
Accommodation
2728 Holiday Homes
Lowest Price
AU$301
Highest Price
AU$2,391

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