Book Holiday Homes in Raymond

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Featured Holiday Homes in Raymond

Sunny Modern Oasis in Portland’s Trendy East End

Sunny Modern Oasis in Portland’s Trendy East End

Portland ME
With a stay at this vacation home, you'll be centrally located in Portland, within a 10-minute drive of Maine Mall and Casco Bay.
Opens in a new windowSunny Modern Oasis in Portland’s Trendy East End
Waterfront, dog-friendly home on 12+ acres with dock, hot tub & sunset views

Waterfront, dog-friendly home on 12+ acres with dock, hot tub & sunset views

Poland ME
Located in Poland, this vacation home is on the waterfront, within a 15-minute drive of Tripp Pond and The Willows Flea Market.
Opens in a new windowWaterfront, dog-friendly home on 12+ acres with dock, hot tub & sunset views
Large, light filled 4 bedroom house - walk to ocean and ferry

Large, light filled 4 bedroom house - walk to ocean and ferry

Peaks Island ME
With a stay at this vacation home in Peaks Island, you'll be by the ocean, just a 1-minute walk from Casco Bay and 7 minutes by foot from Umbrella Cover ...
Opens in a new windowLarge, light filled 4 bedroom house - walk to ocean and ferry
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Bright & breezy beach house w/ private backyard, central AC, & relaxing hot tub

Bright & breezy beach house w/ private backyard, central AC, & relaxing hot tub

Old Orchard Beach ME
With a stay at this vacation home, you'll be centrally located in Old Orchard Beach, within a 10-minute drive of Engine and Harmon Historical Museum.
Opens in a new windowBright & breezy beach house w/ private backyard, central AC, & relaxing hot tub
The Eagle's Nest ♦ Rooftop Deck ♦ Close to Beach

The Eagle's Nest ♦ Rooftop Deck ♦ Close to Beach

Old Orchard Beach ME
With a stay at this vacation home in Old Orchard Beach, you'll be within a 10-minute drive of Engine and Harmon Historical Museum.
Opens in a new windowThe Eagle's Nest ♦ Rooftop Deck ♦ Close to Beach
Private 3BR waterfront home, hot tub, pool table, sandy beach, BBQ, w/d, wifi

Private 3BR waterfront home, hot tub, pool table, sandy beach, BBQ, w/d, wifi

Scarborough ME
With a stay at this vacation home in Scarborough, you'll be on the waterfront, within a 10-minute drive of Maine Mall and Nonesuch River Golf Club.
Opens in a new windowPrivate 3BR waterfront home, hot tub, pool table, sandy beach, BBQ, w/d, wifi
ENJOY YOUR SUMMER AT BEACH ROSE COTTAGE IN OLD ORCHARD BEACH!

ENJOY YOUR SUMMER AT BEACH ROSE COTTAGE IN OLD ORCHARD BEACH!

Old Orchard Beach ME
With a stay at this vacation home, you'll be centrally located in Old Orchard Beach, within a 10-minute drive of Engine and Harmon Historical Museum.
Opens in a new windowENJOY YOUR SUMMER AT BEACH ROSE COTTAGE IN OLD ORCHARD BEACH!
Chic 3-bedroom house in Munjoy Hill with off-street parking.

Chic 3-bedroom house in Munjoy Hill with off-street parking.

2 out of 5
Portland ME
The price is AU$595 per night from 28 Dec to 29 Dec
AU$595
28 Dec - 29 Dec
includes taxes & fees
With a stay at this vacation home in Portland (Munjoy Hill), you'll be within a 10-minute drive of Maine Mall and Casco Bay.
Opens in a new windowChic 3-bedroom house in Munjoy Hill with off-street parking.
Sensational Beachfront Property Old Orchard Beach, with indoor elevator

Sensational Beachfront Property Old Orchard Beach, with indoor elevator

Old Orchard Beach ME
With a stay at this vacation home in Old Orchard Beach, you'll be on the beach, within a 10-minute drive of Engine and Old Orchard Beach.
Opens in a new windowSensational Beachfront Property Old Orchard Beach, with indoor elevator
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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.

Raymond Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Raymond vacation homes are the perfect way for you to wing it.

Holiday houses in Raymond let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Raymond in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Raymond adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Raymond with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Raymond vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Raymond Holiday Homes essential information

Accommodation
755 Holiday Homes
Lowest Price
AU$110
Highest Price
AU$595
Popular accommodation
Sunny Modern Oasis in Portland’s Trendy East End, Waterfront, dog-friendly home on 12+ acres with dock, hot tub & sunset views, Large, light filled 4 bedroom house - walk to ocean and ferry, Bright & breezy beach house w/ private backyard, central AC, & relaxing hot tub, The Eagle's Nest ♦ Rooftop Deck ♦ Close to Beach, Private 3BR waterfront home, hot tub, pool table, sandy beach, BBQ, w/d, wifi, ENJOY YOUR SUMMER AT BEACH ROSE COTTAGE IN OLD ORCHARD BEACH!, Chic 3-bedroom house in Munjoy Hill with off-street parking. , Sensational Beachfront Property Old Orchard Beach, with indoor elevator

Top trending hotels in Raymond

Sebago Lake Cottage on Raymond Cape

Sebago Lake Cottage on Raymond Cape

Raymond ME
With a stay at this cabin in Raymond, you'll be a 1-minute walk from Sebago Lake and 12 minutes by foot from Jordan Bay.
Opens in a new windowSebago Lake Cottage on Raymond Cape
Tru by Hilton Portland Airport Area

Tru by Hilton Portland Airport Area

2.5 out of 5
369 Maine Mall Road South Portland ME
Fully refundableReserve now, pay when you stay
The price is AU$110 per night from 11 Jan to 12 Jan
AU$110
11 Jan - 12 Jan 2026
includes taxes & fees
When you stay at Tru by Hilton Portland Airport Area in South Portland, you'll be near the airport, just steps from Maine Mall and a 3-minute drive from Nonesuch ...
Opens in a new windowTru by Hilton Portland Airport Area
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
468 Fore Street Portland ME
Fully refundableReserve now, pay when you stay
The price is AU$235 per night from 24 Dec to 25 Dec
AU$235
24 Dec - 25 Dec
includes taxes & fees
With a stay at Portland Harbor Hotel, you'll be centrally located in Portland, within a 10-minute drive of Maine Mall and Casco Bay.
Opens in a new windowPortland Harbor Hotel
Save an average of 15% on thousands of hotels when you're signed in
Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

3.5 out of 5
20 Milk Street Portland ME
With a stay at Portland Regency Hotel & Spa, you'll be centrally located in Portland, within a 10-minute drive of Maine Mall and Casco Bay.
Opens in a new windowPortland Regency Hotel & Spa
Don't see what you're looking for?
See all available properties in Raymond
View all properties
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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.