Book Holiday Homes in Raymond

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Featured Holiday Homes in Raymond

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

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

Cumberland
With a stay at this vacation home, you'll be centrally located in Cumberland Center, within a 15-minute drive of Thompson's Point and LL Bean Flagship ...
Cozy & Secluded Estate on 7 acres, Boasting Fresh Renovations!
The Globe House on Munjoy Hill - Walk to Breweries

The Globe House on Munjoy Hill - Walk to Breweries

Portland
With a stay at this vacation home, you'll be centrally located in Portland, within a 10-minute drive of Thompson's Point and Maine Mall.
The Globe House on Munjoy Hill - Walk to Breweries
Rent a room in the gorgeous Holt House

Rent a room in the gorgeous Holt House

Portland
With a stay at this vacation home in Portland (Parkside), you'll be a 3-minute drive from Thompson's Point and 8 minutes from Maine Mall.
Rent a room in the gorgeous Holt House
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Maine Cottage

Maine Cottage

Lyman
Located in Alfred, this vacation home is on a lake, within a 15-minute drive of Swan Pond and Kennebunk Pond.
Maine Cottage
Private Lakefront Estate with 180 Degree Views

Private Lakefront Estate with 180 Degree Views

Raymond
With a stay at this vacation home in Raymond, you'll be steps from Sebago Lake and Jordan Bay.
Private Lakefront Estate with 180 Degree Views
Spacious Country Home Freeport, Only 5 min to LL Bean!

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

Freeport
The price is AU$1,003 per night from 24 Apr to 25 Apr
AU$1,003
includes taxes & fees
24 Apr - 25 Apr
With a stay at this vacation home in Freeport, you'll be by the sea, within a 10-minute drive of LL Bean Flagship Store and Casco Bay.
Spacious Country Home Freeport, Only 5 min to LL Bean!
Ultimate Pine Point Beach Family Compound-4 Units, 8 Bedrooms, Yard

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

Scarborough
The price is AU$4,541 per night from 19 May to 20 May
AU$4,541
includes taxes & fees
19 May - 20 May
With a stay at this vacation home in Scarborough (Grand Beach), you'll be within a 5-minute drive of Old Orchard Beach and Old Orchard Beach Pier.
Ultimate Pine Point Beach Family Compound-4 Units, 8 Bedrooms, Yard
Elegant condo - walk to Portland's best restaurants & Old Port

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

Portland
The price is AU$673 per night from 22 Apr to 23 Apr
AU$673
includes taxes & fees
22 Apr - 23 Apr
With a stay at this vacation home, you'll be centrally located in Portland, a 5-minute drive from Thompson's Point and 9 minutes from Maine Mall.
Elegant condo - walk to Portland's best restaurants & Old Port
Prime City Living Townhouse by RedAwning

Prime City Living Townhouse by RedAwning

2 out of 5
75 Carleton St, Portland, ME
Fully refundable
The price is AU$862 per night from 22 Apr to 23 Apr
AU$862
includes taxes & fees
22 Apr - 23 Apr
With a stay at this vacation home in Portland (Parkside), you'll be a 4-minute drive from Thompson's Point and 8 minutes from Maine Mall.
Prime City Living Townhouse by RedAwning
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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
767 Holiday Homes
Lowest Price
AU$152
Highest Price
AU$4,541
Popular accommodation
Cozy & Secluded Estate on 7 acres, Boasting Fresh Renovations!, The Globe House on Munjoy Hill - Walk to Breweries, Rent a room in the gorgeous Holt House, Maine Cottage, Private Lakefront Estate with 180 Degree Views, Spacious Country Home Freeport, Only 5 min to LL Bean!, Ultimate Pine Point Beach Family Compound-4 Units, 8 Bedrooms, Yard, Elegant condo - walk to Portland's best restaurants & Old Port, Prime City Living Townhouse by RedAwning

Top trending hotels in Raymond

6 bedroom waterfront cabin -enjoy beautiful sunsets!

6 bedroom waterfront cabin -enjoy beautiful sunsets!

Frye Island
With a stay at this vacation home in Raymond, you'll be on the waterfront, just steps from Sebago Lake.
6 bedroom waterfront cabin -enjoy beautiful sunsets!
The Westin Portland Harborview

The Westin Portland Harborview

4 out of 5
157 High St, Portland, ME
Fully refundableReserve now, pay when you stay
The price is AU$236 per night from 28 Apr to 29 Apr
AU$236
includes taxes & fees
28 Apr - 29 Apr
With a stay at The Westin Portland Harborview, you'll be centrally located in Portland, steps from State Theatre and Portland Museum of Art.
The Westin Portland Harborview
La Quinta Inn & Suites by Wyndham Portland

La Quinta Inn & Suites by Wyndham Portland

2.5 out of 5
340 Park Ave, Portland, ME
Fully refundableReserve now, pay when you stay
The price is AU$152 per night from 27 Apr to 28 Apr
AU$152
includes taxes & fees
27 Apr - 28 Apr
Located in Portland, La Quinta Inn & Suites by Wyndham Portland is a 5-minute walk from Portland Exposition Building and 5 minutes by foot from Hadlock ...
La Quinta Inn & Suites by Wyndham Portland
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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$350 per night from 8 May to 9 May
AU$350
includes taxes & fees
8 May - 9 May
With a stay at Portland Harbor Hotel, you'll be centrally located in Portland, a 5-minute drive from Thompson's Point and 9 minutes from Maine Mall.
Portland Harbor Hotel
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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.

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^Subject to availability and chosen travel dates.