Raymond Holiday Rentals

Save an average of 15% on thousands of properties with Expedia Rewards

Most properties are fully refundable. Because flexibility matters.

Search over 2.9 million properties and 550 airlines worldwide

Holiday Rentals in Raymond

Refurbished waterfront 1950s cabin with sauna, firepit, grill & kayaks - dogs ok
10.0 out of 10, Exceptional, (4)
"We had a very nice stay cabin met all our needs"
Refurbished waterfront 1950s cabin with sauna, firepit, grill & kayaks - dogs ok
Authentic with Luxury Amenities With 250 Ft Of Private Sandy Frontage On Sebago
10.0 out of 10, Exceptional, (51)
"This was our third time staying at this camp. And we have loved everyone of them and had no problems whatsoever. Look forward to coming back again again it is the most awesome camp ever. Thanks, Joe."
Authentic with Luxury Amenities With 250 Ft Of Private Sandy Frontage On Sebago
Sensational House on Sebago Lake, Raymond, ME
10.0 out of 10, Exceptional, (33)
"Lovely property and location. Very clean with a fully stocked home. Will certainly be rebooking. Thank you!"
Sensational House on Sebago Lake, Raymond, ME
Save an average of 15% on thousands of hotels when you're signed in
Completely remodeled 2 bedroom apartment in Portland's West End
10.0 out of 10, Exceptional, (35)
"We very much enjoyed our stay at this location. The stairs were a bit scary, but with the light on, you'll be fine. :) Cozy spot for the three of us, well appointed and in a fantastic area. Very walkable, even down to the wharf. We are from a very non-walkable area, so it was amazing to see all the activity and places we could go just walking a bit. We enjoyed our first time in Maine, and can't wait to get back for a longer trip. Thanks to the hosts!"
The price is NZ$678
includes taxes & fees
21 May - 22 May
Completely remodeled 2 bedroom apartment in Portland's West End
Artsy Apt/Private Rooftop Deck!/Old Port Arts Dist
10.0 out of 10, Exceptional, (15)
"This was a great spot for a weekend away! The unit is well equipped with higher end finishes and furnishings which makes the u it well worth visiting. The roof deck was a lovely addition as well! We left on Sunday so was happy to be able to move the car close to the unit Saturday evening to make packing a breeze."
Artsy Apt/Private Rooftop Deck!/Old Port Arts Dist
Glorious getaway on Portland's Eastern Promenade.
10.0 out of 10, Exceptional, (124)
"We really enjoyed our stay. We loved being able to walk to the Eastern Promenade. The beds, including the sofa bed were very comfortable. Very cute and cozy There are stairs to enter the building for anyone with mobility issues. If you are unfamiliar with older buildings, the radiators do make some noise while heating in the winter."
The price is NZ$498
includes taxes & fees
16 May - 17 May
Glorious getaway on Portland's Eastern Promenade.
Cozy, Elegant and Bright 2 bed in the East End
10.0 out of 10, Exceptional, (25)
"The house is located in a nice neighborhood, just two blocks from the water and walkable to downtown. Check in was easy. The apartment is filled with light and very clean. If you happen to be up at dawn the living room windows face east providing a wonderful sunrise view. Would definitely stay there again!"
The price is NZ$604
includes taxes & fees
23 May - 24 May
Cozy, Elegant and Bright 2 bed in the East End
Relaxing loft style cabin getaway for 2. relax and enjoy!
10.0 out of 10, Exceptional, (273)
"This place is perfect for couples! Private, romantic and outdoor lovers dream! I cannot say enough! The pond is gorgeous and fishing access is wonderful! If the place comes up for sale we'll buy it!"
Relaxing loft style cabin getaway for 2. relax and enjoy!
Beach House ∆ Prime Location ∆ Steps to the Ocean
10.0 out of 10, Exceptional, (35)
"The cottage was very nice but the write-up was a little misleading. For example ocean views are very limited—mostly see rooftops, half bath was on ground floor, and stairs to main living area."
The price is NZ$973
includes taxes & fees
19 May - 20 May
Beach House ∆ Prime Location ∆ Steps to the Ocean
The Globe House on Munjoy Hill - Amazing Sunsets - Walk to Breweries
10.0 out of 10, Exceptional, (51)
"Comfortable, clean, very well decorated apartment in a pleasant, walkable neighborhood. I highly recommend this property."
The Globe House on Munjoy Hill - Amazing Sunsets - Walk to Breweries
Whether With Family or Friends Shop, Sight See & Dine at Great Restaurants
9.8 out of 10, Exceptional, (88)
"We had a great time and this rental was very clean. The host was wonderful and easy to communicate with. My only tiny complaint is that the bedroom radiator was really loud (as they tend to be) and I am a light sleeper, so they kept me up. Not any fault of the rental, just is what it is. 15 minute walk to everything. Lovely, overall."
The price is NZ$880
includes taxes & fees
23 May - 24 May
Whether With Family or Friends Shop, Sight See & Dine at Great Restaurants
Charming 110-year former Inn 10' from the Ocean!
9.8 out of 10, Exceptional, (99)
"Lovely home in a beautiful location. Very welcoming, cozy, and friendly. Easy check-in and check-out process. The owner was very accommodating and helpful. Made amazing memories and look forward to returning soon. Thank you so much!"
Charming 110-year former Inn 10' from the Ocean!
Gorgeous ocean-front home with stunning beach views
9.6 out of 10, Exceptional, (74)
"Great little condo. Right on the beach! Balcony is wonderful, as is the view from the master. Second bedroom is definitely a “kids” room with the two bunk beds. Garage was great for a car, would not fit the height of a truck"
Gorgeous ocean-front home with stunning beach views
Bliss Beach House ♦ Huge Ocean View Rooftop Deck ♦
9.6 out of 10, Exceptional, (10)
"This place is just as nice as it looks in the pictures! My friends and I had a blast! What we appreciated the most was how communicative Jason was with us, and how welcome he made us feel! 10/10 recommend. Awesome place! :)"
The price is NZ$1,027
includes taxes & fees
20 May - 21 May
Bliss Beach House ♦ Huge Ocean View Rooftop Deck ♦
Magical Lakeview Cottage on Frye Island, ME
9.4 out of 10, Exceptional, (12)
"Very nice and quiet!"
Magical Lakeview Cottage on Frye Island, ME
Elegant condo - walk to Portland's best restaurants & Old Port
9.4 out of 10, Exceptional, (45)
"The kitchen was very well equipped. Living room was so cozy with the fire. Bed was super comfortable. The unit has really tall ceilings and is cozy. Only issue was the dog upstairs. They kept barking and whining."
Elegant condo - walk to Portland's best restaurants & Old Port
Spacious & Sunny 4 Bedroom Close to Downtown, hot tub
9.4 out of 10, Exceptional, (21)
"Stayed for a weekend for bachelorette party! Very clean, close to downtown and loved the hot tub."
Spacious & Sunny 4 Bedroom Close to Downtown, hot tub
100 feet from the ocean 3 bedroom cottage 420 friendly
9.2 out of 10, Wonderful, (13)
"The property was great and a very convenient location to the beach, shops, and pier. They have everything you could possibly need except food and clothing! Very clean, TVs and ACs in every room. The only challenge as others mentioned is parking. It is a tight fit and if your tires are on the sidewalk you can be ticketed. On our second to last day we were approached by the parking patrol and told this. He was super nice and said he wouldn't ticket us but another may. I said we were leaving the...
100 feet from the ocean 3 bedroom cottage 420 friendly
Large 2BD cottage 10 min to Pier & Beach Pets ok
9.2 out of 10, Wonderful, (15)
"The house was cozy and well equipped. We had a wonderful time."
The price is NZ$464
includes taxes & fees
20 May - 21 May
Large 2BD cottage 10 min to Pier & Beach Pets ok
Lovely home on Crystal Lake with private dock, lake views, deck, & grill
9.0 out of 10, Wonderful, (18)
"This is an ideal location for a fun getaway for any season. Plenty of room for a large/extended family. While there is a road between the house and lake it didn’t detract from the experience at all. Pro tip, in cooler seasons turn on the ceiling fans to push the warmer air down. Otherwise the main room will feel cold. The dock is slightly off level and a couple doors don’t latch completely but those are just signs of a well loved camp."
Lovely home on Crystal Lake with private dock, lake views, deck, & grill
Don't see what you're looking for?
See all available properties in Raymond
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.

Other types of properties in Raymond you may be interested in

Authentic with Luxury Amenities With 250 Ft Of Private Sandy Frontage On Sebago
10.0 out of 10, Exceptional, (51)
"This was our third time staying at this camp. And we have loved everyone of them and had no problems whatsoever. Look forward to coming back again again it is the most awesome camp ever. Thanks, Joe."
Authentic with Luxury Amenities With 250 Ft Of Private Sandy Frontage On Sebago
Portland Harbor Hotel
4.0 star property
9.0 out of 10, Wonderful, (1187)
"Rooms are nice, beds a little too hard, employees not very friendly. I did like you can get coffee in the morning in the lobby. Breakfast not so good. "
The price is NZ$344
includes taxes & fees
19 May - 20 May
Portland Harbor Hotel
The Westin Portland Harborview
4.0 star property
8.6 out of 10, Excellent, (1054)
"The Westin is very conveniently located in downtown Portland. Great harbor view and wonderful staff."
The price is NZ$286
includes taxes & fees
28 May - 29 May
The Westin Portland Harborview
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.

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.

How many holiday rentals are there in Raymond?

With 78 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?

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