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Compare 783 Vacation Homes in Raymond with updated reviews, rates, and availability.

Cozy & Secluded Estate on 7 acres, Boasting Fresh Renovations!

8.2 out of 10, Very Good, (50)
"We had a large group and had more than enough beds and plenty of space to hang out. Would recommend for a big group or a family looking to spread out!"
Cozy & Secluded Estate on 7 acres, Boasting Fresh Renovations!

The Globe House on Munjoy Hill - Walk to Breweries

10.0 out of 10, Exceptional, (77)
"Great historic house in a terrific location. "
The Globe House on Munjoy Hill - Walk to Breweries

Rent a room in the gorgeous Holt House

8.0 out of 10, Very Good, (14)
"Really cool room and in a great location only a short walk from restaurants and sights. "
Rent a room in the gorgeous Holt House

Maine Cottage

9.8 out of 10, Exceptional, (75)
"Second time staying at this property and will definitely stay again !!! "
Maine Cottage

Private Lakefront Estate with 180 Degree Views

Private Lakefront Estate with 180 Degree Views

Spacious Country Home Freeport, Only 5 min to LL Bean!

9.8 out of 10, Exceptional, (12)
"We loved everything about this place. Beautiful, large home, plenty of room for 8 adults and 2 children. Large dining room for meals and family game time. So close to Freeport and all the shopping. Very clean, and the home has everything we needed. We can’t wait to go again!"
Spacious Country Home Freeport, Only 5 min to LL Bean!

Ultimate Pine Point Beach Family Compound-4 Units, 8 Bedrooms, Yard

The price is AED 5,693
AED 10,453 total
includes taxes & fees
8 May - 9 May
Ultimate Pine Point Beach Family Compound-4 Units, 8 Bedrooms, Yard

Elegant condo - walk to Portland's best restaurants & Old Port

9.4 out of 10, Exceptional, (60)
"Great location, walkable to everything we wanted to do in Portland"
The price is AED 588
AED 1,534 total
includes taxes & fees
11 May - 12 May
Elegant condo - walk to Portland's best restaurants & Old Port

Prime City Living Townhouse by RedAwning

2.0 star property
9.0 out of 10, Wonderful, (2)
"It was very convenient. "
The price is AED 678
AED 1,989 total
includes taxes & fees
12 May - 13 May
Prime City Living Townhouse by RedAwning

Fun Family House w/Free WiFi and Furnished Patio - Short Walk to the Beach

7.4 out of 10, Good, (11)
"Clean, pleasant stay with plenty of beds for our entire crew. Thank you."
Fun Family House w/Free WiFi and Furnished Patio - Short Walk to the Beach

Whispering Waters Farmhouse/Barn

Whispering Waters Farmhouse/Barn

Welcome to Happy Place on Peaks Island

10.0 out of 10, Exceptional, (39)
"Lovely cottage."
Welcome to Happy Place on Peaks Island

Convenient Portland home 3 miles from Downtown

10.0 out of 10, Exceptional, (21)
"The reclining furniture was our favorite after running around all day! Very comfortable beds! Great place to stay!"
Convenient Portland home 3 miles from Downtown

Huge Historic Downtown Townhome

10.0 out of 10, Exceptional, (1)
"From California, I put together a 21st birthday weekend in Portland for my daughter and five of her friends from Bates College. Tim, the manager, was communicative, helpful, and always available. The townhome is adorable, and the location is fantastic."
The price is AED 976
AED 1,696 total
includes taxes & fees
12 May - 13 May
Huge Historic Downtown Townhome

Cozy four-season getaway on Pettingill Pond

Cozy four-season getaway on Pettingill Pond

Luxurious Penthouse with Modern Design in Downtown

9.6 out of 10, Exceptional, (7)
"We had an amazing stay and it was an immense pleasure to call this charming place homebase for a long weekend during the holidays and a family wedding! Many thanks to the owners for hosting us!!"
Luxurious Penthouse with Modern Design in Downtown

New Well Built Elegant Home on the Water 2 miles to Freeport, 9 to Portland!

9.8 out of 10, Exceptional, (178)
"What a beautiful home and location! Second time we have stayed here and love it. "
New Well Built Elegant Home on the Water 2 miles to Freeport, 9 to Portland!

Stealing Time at OOB with a 8 minute walk to the Beach!

10.0 out of 10, Exceptional, (16)
"All as advertised. Clean, convenient, easy walk to the beach and boardwalk."
Stealing Time at OOB with a 8 minute walk to the Beach!

Beautifully built Cape Elizabeth home nestled in the woods on 2.5 acres

10.0 out of 10, Exceptional, (15)
"This house is beautifully designed and ideal for a family vacation. We had a wonderful stay, and Jocelyn, our host, made everything easy to navigate, always being available for any questions we had. "
Beautifully built Cape Elizabeth home nestled in the woods on 2.5 acres

Beachwood Cottage by Bayley Vacation Rentals

10.0 out of 10, Exceptional, (11)
"This house is wonderful, with a great back yard and quick walk to the beach. Our family loved staying here and looking forward to booking again!"
Beachwood Cottage by Bayley Vacation Rentals
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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Other property types in Raymond

6 bedroom waterfront cabin -enjoy beautiful sunsets!

9.8 out of 10, Exceptional, (18)
"John was a phenomenal host and made sure we had all the necessary resources and information for an amazing getaway. His house has spectacular views and all the amenities that a person could ask for. Don't HESITATE BOOK NOW!"
6 bedroom waterfront cabin -enjoy beautiful sunsets!

Refurbished waterfront 1950s cabin with sauna, firepit, grill & kayaks - dogs ok

7.6 out of 10, Good, (10)
"The view , the quiet, the autumn colors ,"
Refurbished waterfront 1950s cabin with sauna, firepit, grill & kayaks - dogs ok

The Weldon Hotel

4.5 star property
9.8 out of 10, Exceptional, (57)
"Great hotel"
The price is AED 773
AED 1,118 total
includes taxes & fees
14 May - 15 May
The Weldon Hotel
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.