Raymond Holiday Rentals

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Check prices for these dates

Tonight
30 Dec - 31 Dec
Tomorrow
31 Dec - 1 Jan
This weekend
2 Jan - 4 Jan
Next weekend
9 Jan - 11 Jan

Our top choices for Raymond holiday rentals

Fridge, microwave, oven, stovetop
Pine Point Beach private, quaint, charming studio.

Pine Point Beach private, quaint, charming studio.

Pine Point Beach private, quaint, charming studio.
2.0 star property
Blue Point
10.0 out of 10, Exceptional, (25)
"Cozy, clean and comfortable! Perfect weekend beach get away! "
United States
jen e.
The price is HK$684
HK$1,627 total
includes taxes & fees
1 Jan - 2 Jan 2026
Pine Point Beach private, quaint, charming studio.
Dining
Sunny Spot with Private Parking.

Sunny Spot with Private Parking.

Sunny Spot with Private Parking.
2.0 star property
Knightville
9.8 out of 10, Exceptional, (25)
"Cute property.. also really suitable for long stay as the amenities were complete and near groceries and some restaurants and cafes.. convenient!"
United States
Giana
The price is HK$754
HK$1,551 total
includes taxes & fees
4 Jan - 5 Jan 2026
Sunny Spot with Private Parking.
Terrace/patio
Modern, Luxurious, Cabin in the Woods - 17

Modern, Luxurious, Cabin in the Woods - 17

Modern, Luxurious, Cabin in the Woods - 17
Freeport
10.0 out of 10, Exceptional, (3)
"Awesome camping in a great, quiet campground. The staff is very responsive and all the little details make this place special."
United States
Miranda K.
The price is HK$1,306
HK$2,305 total
includes taxes & fees
4 Jan - 5 Jan 2026
Modern, Luxurious, Cabin in the Woods - 17
Outdoor dining
Peaceful & minutes from the Old Port with private parking

Peaceful & minutes from the Old Port with private parking

Peaceful & minutes from the Old Port with private parking
Knightville
9.8 out of 10, Exceptional, (7)
"This well- appointed apartment was perfect for our stay in the Portland area. Jennifer was always quick to answer any questions. We would definitely recommend this listing."
United States
Lynn E.
The price is HK$762
HK$1,669 total
includes taxes & fees
6 Jan - 7 Jan 2026
Peaceful & minutes from the Old Port with private parking
1 bedroom, free WiFi, bed sheets
Cute Intown suite

Cute Intown suite

Cute Intown suite
Auburn
9.6 out of 10, Exceptional, (8)
"From the booking to the stay, it’s been perfect!"
United States
Mary F.
Cute Intown suite
Outdoor dining
Waterfront Access with Kayaks, Private Deck and a Firepit

Waterfront Access with Kayaks, Private Deck and a Firepit

Waterfront Access with Kayaks, Private Deck and a Firepit
2.0 star property
Gray
10.0 out of 10, Exceptional, (3)
" The place was wonderful!! Very peaceful and beautiful!! "
United States
Anonymous traveller
The price is HK$1,042
HK$5,283 total
includes taxes & fees
5 Jan - 6 Jan 2026
Waterfront Access with Kayaks, Private Deck and a Firepit
3 bedrooms, desk, iron/ironing board, travel cot
3BR Coastal Gem with a 5 Min Drive to Ocean Fun

3BR Coastal Gem with a 5 Min Drive to Ocean Fun

3BR Coastal Gem with a 5 Min Drive to Ocean Fun
Old Orchard Beach
10.0 out of 10, Exceptional, (6)
"I loved that the hosts live nearby and responded quickly when we needed anything. Having a washer and dryer onsite is great for longer stays. Beds were comfortable and plenty of blankets and pillows. Highly recommend this property."
United States
Terry
The price is HK$847
HK$2,745 total
includes taxes & fees
4 Jan - 5 Jan 2026
3BR Coastal Gem with a 5 Min Drive to Ocean Fun
Exterior
Cozy, Elegant and Bright 2 bed in the East End

Cozy, Elegant and Bright 2 bed in the East End

Cozy, Elegant and Bright 2 bed in the East End
Munjoy Hill
9.8 out of 10, Exceptional, (52)
"Great location and cozy."
United States
Heather G.
The price is HK$714
HK$1,786 total
includes taxes & fees
4 Jan - 5 Jan 2026
Cozy, Elegant and Bright 2 bed in the East End
1 bedroom, WiFi, bed sheets
Studio Apartment near downtown Walkable!

Studio Apartment near downtown Walkable!

Studio Apartment near downtown Walkable!
West Bayside
8.4 out of 10, Very good, (7)
"The summary and the pictures shown are exactly what you’re going to get. The owner did a good job with the description, I "
United States
Alexandria T.
The price is HK$490
HK$1,048 total
includes taxes & fees
9 Jan - 10 Jan 2026
Studio Apartment near downtown Walkable!
Interior
Adorable Portland getaway on the Eastern Promenade

Adorable Portland getaway on the Eastern Promenade

Adorable Portland getaway on the Eastern Promenade
Munjoy Hill
9.6 out of 10, Exceptional, (128)
"The place was perfect. It was right in the middle of everything and a perfe spot for a getaway"
United States
Jon S.
The price is HK$855
HK$1,576 total
includes taxes & fees
4 Jan - 5 Jan 2026
Adorable Portland getaway on the Eastern Promenade
1 bedroom, desk, free WiFi, bed sheets
Spacious Studio Near Sebago Lake

Spacious Studio Near Sebago Lake

Spacious Studio Near Sebago Lake
2.0 star property
Windham
10.0 out of 10, Exceptional, (4)
"Host was very welcoming and check in was simple "
United States
Michael C.
The price is HK$760
HK$998 total
includes taxes & fees
1 Jan - 2 Jan 2026
Spacious Studio Near Sebago Lake
Smart TV
Beautiful 1st Floor Apartment & Amazing Shower

Beautiful 1st Floor Apartment & Amazing Shower

Beautiful 1st Floor Apartment & Amazing Shower
Parkside
9.0 out of 10, Wonderful, (26)
"This was a clean and good location for our stay. "
United States
Jocelyn R.
The price is HK$547
HK$1,232 total
includes taxes & fees
4 Jan - 5 Jan 2026
Beautiful 1st Floor Apartment & Amazing Shower
Interior
Rustic Charm Meets Modern Luxury: Stylish 2BR, 1BA Apartment

Rustic Charm Meets Modern Luxury: Stylish 2BR, 1BA Apartment

Rustic Charm Meets Modern Luxury: Stylish 2BR, 1BA Apartment
Auburn
9.6 out of 10, Exceptional, (8)
"10 out of 10. Would highly recommend! Hosts are amazing, apartment is amazing and location is great."
United States
Lora L.
The price is HK$949
HK$2,822 total
includes taxes & fees
4 Jan - 5 Jan 2026
Rustic Charm Meets Modern Luxury: Stylish 2BR, 1BA Apartment
Beach nearby
Arlie`s Digs! - One Block To Willard Beach!

Arlie`s Digs! - One Block To Willard Beach!

Arlie`s Digs! - One Block To Willard Beach!
Willard Beach
10.0 out of 10, Exceptional, (63)
"We had a wonderful week here. Fantastic proximity to the beach & a great bakery and ice cream shop. They accommodated us and our dog very well and had everything we need for a great stay. "
United States
Elizabeth C.
The price is HK$1,201
HK$2,749 total
includes taxes & fees
4 Jan - 5 Jan 2026
Arlie`s Digs! - One Block To Willard Beach!
3 bedrooms, premium bedding, iron/ironing board, travel cot
Cozy 3BR | Pet Friendly | Near Portland | Parking

Cozy 3BR | Pet Friendly | Near Portland | Parking

Cozy 3BR | Pet Friendly | Near Portland | Parking
Westbrook
10.0 out of 10, Exceptional, (12)
"We had a great stay here. It was very clean and conveniently located."
United States
Angela B.
The price is HK$972
HK$2,957 total
includes taxes & fees
5 Jan - 6 Jan 2026
Cozy 3BR | Pet Friendly | Near Portland | Parking
Exterior detail
Updated 2 BD cottage. 10 min walk to Pier & Beach sleeps 5

Updated 2 BD cottage. 10 min walk to Pier & Beach sleeps 5

Updated 2 BD cottage. 10 min walk to Pier & Beach sleeps 5
Old Orchard Beach
8.0 out of 10, Very good, (24)
"Was the perfect place to unwind. Close enough to walk to beach, restaurants and shops. Enjoyed our stay emensly!"
United States
Maria H.
The price is HK$777
HK$1,678 total
includes taxes & fees
5 Jan - 6 Jan 2026
Updated 2 BD cottage. 10 min walk to Pier & Beach sleeps 5
Property grounds
Manor Suite,cozy newly renovated,downtown & beach

Manor Suite,cozy newly renovated,downtown & beach

Manor Suite,cozy newly renovated,downtown & beach
Bridgton
10.0 out of 10, Exceptional, (1)
"Property was very clean! it had everything you needed right there! "
United States
Lisa
The price is HK$643
HK$1,251 total
includes taxes & fees
14 Jan - 15 Jan 2026
Manor Suite,cozy newly renovated,downtown & beach
Interior
City Amenities, Casco Bay Sunrises and Natural Beauty

City Amenities, Casco Bay Sunrises and Natural Beauty

City Amenities, Casco Bay Sunrises and Natural Beauty
East Deering
9.8 out of 10, Exceptional, (122)
"Perfect location and the host was immediately repsonsive and always friendly!"
United States
Jon L.
The price is HK$1,119
HK$2,330 total
includes taxes & fees
4 Jan - 5 Jan 2026
City Amenities, Casco Bay Sunrises and Natural Beauty
Interior
The Saco Suite - Downtown, Dog Friendly, Sleeps 4, Walk to Bars & Restaurants!

The Saco Suite - Downtown, Dog Friendly, Sleeps 4, Walk to Bars & Restaurants!

The Saco Suite - Downtown, Dog Friendly, Sleeps 4, Walk to Bars & Restaurants!
Downtown Saco
10.0 out of 10, Exceptional, (18)
"The property was exactly as advertised, and it was a perfect two night stay for us on a road trip up the Maine coast with our dogs. The location was perfect to explore Portland, Saco, Biddeford, and Kennebunkport. The hosts were super responsive and friendly. We would definitely stay here again in future!"
United States
Ryan S.
The price is HK$931
HK$2,336 total
includes taxes & fees
4 Jan - 5 Jan 2026
The Saco Suite - Downtown, Dog Friendly, Sleeps 4, Walk to Bars & Restaurants!
TV
Cozy 1-bedroom apartment in awesome Portland with WiFi, AC

Cozy 1-bedroom apartment in awesome Portland with WiFi, AC

Cozy 1-bedroom apartment in awesome Portland with WiFi, AC
Parkside
8.0 out of 10, Very good, (4)
"Everything was perfect."
United States
Edward J.
The price is HK$470
HK$1,148 total
includes taxes & fees
7 Jan - 8 Jan 2026
Cozy 1-bedroom apartment in awesome Portland with WiFi, AC
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 Raymond Hotel Reviews

Aloft Portland Downtown Waterfront ME

Aloft Portland Downtown Waterfront ME

10/10 Excellent
"Excellent stay - the room was comfortable and the hotel had a great breakfast. The bartender Chris was amazing and shared his personal guide to area restaurants and activities and we tried and enjoyed many things from his list."
Jennifer 2-night trip
Posted 1 day ago
Aloft Portland Downtown Waterfront ME

Find out more about Raymond

Search for holiday rentals in Raymond on Expedia! You can easily find your home rentals, villas, holiday apartments in Raymond using one of the methods below:

  • View our selection of featured holiday rentals in Raymond
  • Use the map to find apartments and other holiday homes in the Raymond neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Raymond while they last

Look no further and take a look at our great range of rental properties in Raymond!

Frequently asked questions

Are there holiday rentals in Raymond?

Yes, there are holiday rentals close to the most popular sights in Raymond, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Raymond has to offer?

Bright & breezy beach house w/ private backyard, central AC, & relaxing hot tub: This holiday home rental outside of Raymond is located in the city centre, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as 1 hot tub.

How many holiday rentals are there in Raymond?

With 82 Expedia holiday rentals, you're guaranteed to find just the right place for your Raymond stay.

What’s there to see and do in Raymond?

Little Sebago Lake and Crescent Lake are a couple of lovely local spots to get outside and enjoy nature. While here, Sebago Lake and Panther Pond are other places worth a visit.

What’s a holiday rental in Raymond like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Raymond. Holiday rentals offer amenities such as laundry facilities and kitchens so you'll feel right at home. If you're concerned about a clean environment, holiday rentals can provide a sense of seclusion away from public hotel lifts and bustling concierge desks while still allowing you to travel. You'll also have more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a popular choice for a small group gathering.